Granted Patent
B2
US 12,396,982 · App. 18/744,484 · Granted Aug 26, 2025
Compositions of matter and pharmaceutical compositions
Assignee:
Atai Therapeutics, Inc.
A61K31/4045A61K9/0043A61K9/06A61K9/2009A61K9/2013A61K9/2018A61K9/2027A61K9/2054A61K9/7061A61K9/7069A61K31/405A61K31/48A61K31/55A61K31/675C07D209/16
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Abstract
Pharmaceutical formulations of novel indole compounds and psilocybin analogs are manufactured, provided in novel oral, transdermal, and nasal pharmaceutical compositions for use to treat neurological, mood or abuse diseases and disorders.
Claims (23)
1. A pharmaceutical product for delivery across a mucosal membrane, wherein said product comprises:
an active ingredient, wherein the active ingredient is DMT or DMT fumarate, or a pharmaceutically acceptable salt of DMT, wherein the active ingredient is present in a therapeutically effective amount; and
a pharmaceutically acceptable carrier,
wherein the active ingredient is capable of crossing a mucosal membrane.
2. The pharmaceutical product of claim 1 , wherein the therapeutically effective amount is about 0.01%-about 20% (w/w).
3. The pharmaceutical product of claim 1 , wherein the mucosal membrane is sublingual, buccal, nasal, or oral.
4. The pharmaceutical product of claim 3 , wherein the pharmaceutical product is in the form of a solution, a gel, a suspension, an emulsion, liposome, or microparticles.
5. The pharmaceutical product of claim 4 , wherein the pharmaceutically acceptable carrier is an adhesive polymer.
6. The pharmaceutical product of claim 4 , wherein the product is in the form of a spray.
7. The pharmaceutical product of claim 4 , wherein the product is in the form of a film.
8. The pharmaceutical product of claim 1 , wherein the active ingredient is DMT or a pharmaceutically acceptable salt thereof.
9. The pharmaceutical product of claim 1 , wherein the active ingredient is DMT fumarate.
10. The pharmaceutical product of claim 8 , further comprising an MAOI.
11. The pharmaceutical product of claim 10 , wherein the MAOI is selected from the group consisting of harmala alkaloids, harmine, harmane, harmaline, hydrazine, iproniazid, isocarboxazid, nialamide, phenelzine, hydracarbazine, tranylcypromine, bifemelane, moclobemide, pirlindole, toloxatone, rasagiline, selegiline, and safinamide.
12. The pharmaceutical product of claim 9 , further comprising an MAOI.
13. The pharmaceutical product of claim 12 , wherein the MAOI is selected from the group consisting of harmala alkaloids, harmine, harmane, harmaline, hydrazine, iproniazid, isocarboxazid, nialamide, phenelzine, hydracarbazine, tranylcypromine, bifemelane, moclobemide, pirlindole, toloxatone, rasagiline, selegiline, and safinamide.
14. The pharmaceutical product of claim 11 , wherein the MAOI is harmine.
15. The pharmaceutical product of claim 13 , wherein the MAOI is harmine.
16. The pharmaceutical product of claim 1 , wherein the pharmaceutical product is an aqueous gel in an amount between about 0.04 ml and about 0.50 mL.
17. The pharmaceutical product of claim 16 , wherein the active ingredient is DMT or a pharmaceutically acceptable salt thereof.
18. The pharmaceutical product of claim 17 , wherein the active ingredient is DMT fumarate.
19. The pharmaceutical product of claim 8 , wherein the pharmaceutical product is in the form of a sublingual strip.
20. The pharmaceutical product of claim 9 , wherein the pharmaceutical product is in the form of a sublingual strip.
Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Feb 20, 2025
From: ATAI LIFE SCIENCES N.V.
To: ATAI THERAPEUTICS, INC.
Reel/Frame 070274/0194 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Feb 20, 2025
From: PSILERA, INC.
To: ATAI LIFE SCIENCES N.V.
Reel/Frame 070274/0210 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Jun 18, 2024
From: WITOWSKI, CHRISTOPHER G.; SALM, JACQUELINE L.
To: TERP LIFE, LLC
Reel/Frame 067753/0637 →
Continuity (6)
Provisional Application
63134805
· Jan 7, 2021
Provisional Application
63106516
· Oct 28, 2020
Provisional Application
63021866
· May 8, 2020
References Cited (400)
US 3499003A
· Welstead, Jr.
· 1970
[cited by applicant]
US 3594391A
· Wolf et al.
· 1971
[cited by applicant]
US 3781300A
· Wolf et al.
· 1973
[cited by applicant]
US 4252803A
· Webb
· 1981
[cited by applicant]
US 5340838A
· Gidda et al.
· 1994
[cited by applicant]
US 5347029A
· Johnson
· 1994
[cited by applicant]
US 5637593A
· Porter et al.
· 1997
[cited by applicant]
US 5705527A
· Ishihara et al.
· 1998
[cited by applicant]
US 6201025B1
· Dax et al.
· 2001
[cited by applicant]
US 6403808B1
· Glennon et al.
· 2002
[cited by applicant]
US 6436950B1
· Achari et al.
· 2002
[cited by applicant]
US 6500456B1
· Capella
· 2002
[cited by applicant]
US 8268856B2
· Hamann et al.
· 2012
[cited by applicant]
US 9388395B2
· Nazor et al.
· 2016
[cited by applicant]
US 9549942B2
· Jo et al.
· 2017
[cited by applicant]
US 20020052370A1
· Barber et al.
· 2002
[cited by applicant]
US 20030079301A1
· Sauter et al.
· 2003
[cited by applicant]
US 20050152858A1
· Bertz et al.
· 2005
[cited by applicant]
US 20050245594A1
· Sutter et al.
· 2005
[cited by applicant]
US 20070099909A1
· Chen et al.
· 2007
[cited by applicant]
US 20080248511A1
· Daily et al.
· 2008
[cited by applicant]
US 20080318957A1
· Glinka et al.
· 2008
[cited by applicant]
US 20090221549A1
· Gerber et al.
· 2009
[cited by applicant]
US 20110245215A1
· Carrara et al.
· 2011
[cited by applicant]
US 20120028995A1
· Ansorge et al.
· 2012
[cited by applicant]
US 20120108510A1
· Young et al.
· 2012
[cited by applicant]
US 20120122948A1
· Soubhye et al.
· 2012
[cited by applicant]
US 20150284365A1
· Elder et al.
· 2015
[cited by applicant]
US 20160106694A1
· Roberts et al.
· 2016
[cited by applicant]
US 20210015738A1
· LaRosa et al.
· 2021
[cited by applicant]
US 20210236523A1
· Schindler et al.
· 2021
[cited by applicant]
US 20210322306A1
· Espinoza et al.
· 2021
[cited by applicant]
US 20210322447A1
· Plakogiannis et al.
· 2021
[cited by applicant]
US 20220024956A1
· Slassi et al.
· 2022
[cited by applicant]
US 20220031662A1
· Terwey
· 2022
[cited by applicant]
US 20220071958A1
· Terwey
· 2022
[cited by applicant]
US 20220079881A1
· Modi
· 2022
[cited by applicant]
US 20220096504A1
· Blumstock et al.
· 2022
[cited by applicant]
US 20220273628A1
· Liechti et al.
· 2022
[cited by applicant]
US 20220304980A1
· Arnold et al.
· 2022
[cited by applicant]
US 20220354824A1
· Witowski et al.
· 2022
[cited by applicant]
US 20230041584A1
· Perni et al.
· 2023
[cited by applicant]
US 20230099972A1
· Rao et al.
· 2023
[cited by applicant]
US 20230136824A1
· Rao et al.
· 2023
[cited by applicant]
US 20230233537A1
· Dornbierer et al.
· 2023
[cited by applicant]
US 20230310374A1
· Rao et al.
· 2023
[cited by applicant]
US 20230322735A1
· Kruegel
· 2023
[cited by applicant]
US 20240116896A1
· Khan et al.
· 2024
[cited by applicant]
US 20240287107A1
· Khan
· 2024
[cited by applicant]
US 20250002457A1
· Yacoub et al.
· 2025
[cited by applicant]
US 20250064783A1
· Witowski et al.
· 2025
[cited by applicant]
EP 0821957A2
· 1998
[cited by applicant]
EP 1336602A1
· 2003
[cited by applicant]
WO WO9506638A1
· 1995
[cited by applicant]
WO WO9524200A1
· 1995
[cited by applicant]
WO WO9617842A1
· 1996
[cited by applicant]
WO WO0041755A1
· 2000
[cited by applicant]
WO WO0051672A1
· 2000
[cited by applicant]
WO WO0211800A2
· 2002
[cited by applicant]
WO WO02068029A2
· 2002
[cited by applicant]
WO WO02068030A2
· 2002
[cited by applicant]
WO WO02068031A2
· 2002
[cited by applicant]
WO WO02068032A2
· 2002
[cited by applicant]
WO WO03000310A2
· 2003
[cited by applicant]
WO WO03020350A1
· 2003
[cited by applicant]
WO WO03026559A2
· 2003
[cited by applicant]
WO WO03082393A1
· 2003
[cited by applicant]
WO WO03084591A1
· 2003
[cited by applicant]
WO WO03090812A2
· 2003
[cited by applicant]
WO WO2006099416A1
· 2006
[cited by applicant]
WO WO2010151258A1
· 2010
[cited by applicant]
WO WO2011041870A1
· 2011
[cited by applicant]
WO 2013063492A1
· 2013
[cited by applicant]
WO 2018064465A1
· 2018
[cited by applicant]
WO 2018081456A1
· 2018
[cited by applicant]
WO WO2018094106A2
· 2018
[cited by applicant]
WO WO2018148605A1
· 2018
[cited by applicant]
WO WO2019081764A1
· 2019
[cited by applicant]
WO WO2019213551A1
· 2019
[cited by applicant]
WO WO2020037372A1
· 2020
[cited by applicant]
WO 2020181194A1
· 2020
[cited by applicant]
WO WO2020169850A1
· 2020
[cited by applicant]
WO WO2020169851A1
· 2020
[cited by applicant]
WO WO2020176597A1
· 2020
[cited by applicant]
WO WO2020212951A1
· 2020
[cited by applicant]
WO 2021003467A1
· 2021
[cited by applicant]
WO 2021168082A1
· 2021
[cited by applicant]
WO WO2021155468A1
· 2021
[cited by applicant]
WO 2021188782A1
· 2021
[cited by applicant]
WO 2021226416A1
· 2021
[cited by applicant]
WO WO2021226041A1
· 2021
[cited by applicant]
WO 2021259962A1
· 2021
[cited by applicant]
WO WO2021244831A1
· 2021
[cited by applicant]
WO WO2021250434A1
· 2021
[cited by applicant]
WO WO2021250435A1
· 2021
[cited by applicant]
WO WO2022051670A1
· 2022
[cited by applicant]
WO WO2022061242A1
· 2022
[cited by applicant]
WO WO2022082058A1
· 2022
[cited by applicant]
WO WO2022109050A1
· 2022
[cited by applicant]
WO WO2022123232A1
· 2022
[cited by applicant]
WO WO2022150675A1
· 2022
[cited by applicant]
WO WO2022160056A1
· 2022
[cited by applicant]
WO WO2022170442A1
· 2022
[cited by applicant]
WO WO2022195011A1
· 2022
[cited by applicant]
WO 2022243285A1
· 2022
[cited by applicant]
WO WO2022232179A1
· 2022
[cited by applicant]
WO WO2022235514A1
· 2022
[cited by applicant]
WO WO2022235529A1
· 2022
[cited by applicant]
WO WO2022246572A1
· 2022
[cited by applicant]
WO WO2022251351A1
· 2022
[cited by applicant]
WO WO2022261383A1
· 2022
[cited by applicant]
WO WO2023283386A2
· 2023
[cited by applicant]
WO WO2023021112A1
· 2023
[cited by applicant]
WO WO2023036473A1
· 2023
[cited by applicant]
WO WO2023055992A1
· 2023
[cited by applicant]
WO 2023076150A1
· 2023
[cited by applicant]
WO WO2023076135A1
· 2023
[cited by applicant]
WO WO2023078604A1
· 2023
[cited by applicant]
WO WO2023111544A2
· 2023
[cited by applicant]
WO WO2023115166A1
· 2023
[cited by applicant]
WO WO2023129956
· 2023
[cited by applicant]
WO WO2024054866A2
· 2024
[cited by applicant]
WO WO2024092106A2
· 2024
[cited by applicant]
WO WO2024118767A2
· 2024
[cited by applicant]
WO WO2024119075A1
· 2024
[cited by applicant]
WO WO2024130140A2
· 2024
[cited by applicant]
WO WO2024130140A3
· 2024
[cited by applicant]
WO WO2024227149A2
· 2024
[cited by applicant]
WO 2024342488A2
· 2024
[cited by applicant]
WO WO2024243488A2
· 2024
[cited by applicant]
WO WO2025019800A1
· 2025
[cited by applicant]
WO WO2025024637A1
· 2025
[cited by applicant]
WO WO2025054397A1
· 2025
[cited by applicant]
(National Center for Biotechnology Information) “[2-bromo-3-[2-(dimethylamino) ethyl]-1H-indol-4-yl] acetate: PUBCHEM CID 157042555” Pubchem entry (online), pp. 1-8, Nov. 30, 2021; Retrieved on Jul. 9, 2024 from the Int…
[cited by applicant]
(National Center for Biotechnology Information) “[3-[2-(dimethylamino) ethyl]-2-fluoro-1H-indol-4-yl]acetate: PUBCHEM CID 162478146” Pubchem entry (online), pp. 1-8, Feb. 6, 2022; Retrieved on Jul. 9, 2024 from the Inte…
[cited by applicant]
(National Center for Biotechnology Information) “3-[2-(dimethylamino) ethyl)-2-fluoro-1H-indol-4-ol: PUBCHEM CID 162478135” Pubchem entry (online), pp. 1-8, Feb. 6, 2022; Retrieved on Jul. 9, 2024 from the Internet: [UR…
[cited by applicant]
(National Center for Biotechnology Information) “1-[3-[2-(dlmethylamino) ethyl]-1H-indol-4-yl]-N-methylmethanesulfonamlde: PUBCHEM CID 149771082” Pubchem entry (online), pp. 1-8, Aug. 12, 2020; Retrieved on Jul. 9, 2024…
[cited by applicant]
(National Center for Biotechnology Information) “4-Acetoxy-N, N-diisopropyltryptamine: PUBCHEM CID 24801868” Pubchem entry (online), pp. 1-19, Jun. 6, 2008; Retrieved on Jul. 9, 2024 from the Internet: [URL: https:f/pub…
[cited by applicant]
(National Center for Biotechnology Information) “N,N-Diisopropyl-4-methoxytryptamine: PUBCHEM CID 24802108” Pubchem entry (online), pp. 1-12, Jun. 6, 2008; Retrieved on Jul. 9, 2024 from theInternet: [URL: https:f/pubch…
[cited by applicant]
(National Center for Biotechnology Information) “[3-[2-[di(propan-2-yl)amino] ethyl)-1H-indol-4-yl) dihydrogen phosphate: Pubchem Cid 166138444” Pubchem entry (online), pp. 1-7. Dec. 20, 2022; Retrieved on Jul. 9, 2024 …
[cited by applicant]
Pubmed Compound Record for CID 84056101, 2-(2-Chloro-4-methoxy-1H-indol-3-yl)ethyanamine, U.S. National Library of Medicine, Oct. 20, 2014, pp. 1-7, (https://pubchem.ncbi.nlm.nih.gov/compound/84056101).
[cited by applicant]
Pubmed Compound Record for CID 123606, Almotriptan, U.S. National Library of Medicine, Aug. 8, 2005 pp. 1-40, (https://pubchem.ncbi.nlm.nih.gov/compound/123606).
[cited by applicant]
Pubmed Compound Record for CID 84058691, 1-(2-Chloro-4-methoxy-1H-indol-3-yl)propan-2-amine, U.S. National Library of Medicine, Oct. 20, 2014, pp. 1-7, (https://pubchem.ncbi.nlm.nih.gov/compound/84058691).
[cited by applicant]
PCT International Search Report, PCT/US2131215 (Oct. 1, 2021).
[cited by applicant]
PCT Written Opinion, PCT/US2131215 (Oct. 1, 2021).
[cited by applicant]
Pubchem, Substance Record for SID 313512691, Available Date Jun. 11, 2016 [retrieved on Dec. 12, 2022] Retrieved from the Internet <URL:https://pubchem.ncbi.nlm.nih.gov/sustance/313512691>.
[cited by applicant]
Pubchem, Substance Record for SID 471368824 Available Date Sep. 27, 2002 [retrieved on Feb. 1, 2023] Retrieved from the Internet <URL:https://pubchem.ncbi.nlm.nih.gov/sustance/471368824>.
[cited by applicant]
Pubchem, Substance Record for SID 474211406 Available Date Dec. 15, 2002 [retrieved on Feb. 1, 2023] Retrieved from the Internet <URL:https://pubchem.ncbi.nlm.nih.gov/sustance/474211406>.
[cited by applicant]
European Patent Office, Extended Search Report, EP Application Serial No. 21800237.6, Apr. 15, 2024.
[cited by applicant]
Database Registry [Online] Chemical Abstract Service, Columbus, Ohio, US; Aug. 2, 2017 (Aug. 2, 2017), retrieved from STN Database accession No. 2107153-36-4.
[cited by applicant]
Lyon R A et al: “Indolealkylamine analogs share 5-HT″2 binding characteristics with phenylalkylamine hallucinogens”,European Journal of Pharmacology, Elsevier Science, NL, vol. 145, No. 3, Jan. 19, 1988, pp. 291-297.
[cited by applicant]
Blough Bruce E et al: “Alpha-ethyltryptamines as dual dopamine serotonin releasers”, Bioorganic & Medicinal Chemistry Letters, Elsevier, Amsterdam NL, vol. 24, No. 19, Jul. 29, 2014, pp. 4754-4758.
[cited by applicant]
University of Zurich. Compositions and kits comprising N,N-dimethyltryptamine and harmine and their use in therapy. European Patent Application Serial No. EP20181489, filing date Jun. 24, 2020, receipt by WIPO Jul. 6, 2…
[cited by applicant]
Huang et al. Nose-to-brain delivery of drug nanocrystals by using Ca2+ responsive deacetylated gellan gum based in situ-nanogel. International Journal of Pharmaceuticals. 2020;S0378-5173(20)31167-4.
[cited by applicant]
Mahalingam. Semisolid Dosages: Ointments, Creams, and Gels. in Pharmaceutical Manufacturing Handbook: Production and Processes. (Chapter 9, 267-312), Shayne C. Gad ed., John Wiley & Sons, Inc. 2008.
[cited by applicant]
1 Japanese Patent Office, Official Action, JP 2022-567840, Nov. 28, 2024.
[cited by applicant]
Abiero et al., “Four Novel Synthetic Tryptamine Analogs Induce Head-Twitch Responses and Increase 5-HTR2a in the Prefrontal Cortex in Mice.” Biomol Ther (Seoul). Jan. 1, 2020; 28(1): 83-91.
[cited by applicant]
Andersson et al., “Psychoactive substances as a last resort—a qualitative study of self-treatment of migraine and cluster headaches.” Harm Reduct J. Sep. 5, 2017; 14(1):60. 11 pages.
[cited by applicant]
Archer et al., “5-Methoxy-N, N-dimethyltryptamine-induced analgesia is blocked by alpha-adrenoceptor antagonists in rats.” Br J Pharmacol. Oct. 1986;89(2):293-8. doi: 10.1111/j.1476-5381.1986.tb10259.x.
[cited by applicant]
Baker et al., “Neurochemical and neuropharmacological investigation of N-cyanoethyltryptamine, a potential prodrug of tryptamine.” Proc West Pharmacol Soc., 1987; 30: 307-11.
[cited by applicant]
Baker et al., “Neuropharmacological and Neurochemical Properties of N-(2-Cyanoethyl)-2-Phenylethylamine, A Prodrug of 2-Phenylethylamine.” Br J Pharmacol. Oct. 1987; 92(2): 243-55.
[cited by applicant]
Banker, G. S., et al., “Modern Pharmaceutics.” Third Edition, Revised, and Expanded, Marcel Dekker, Inc. (1996); pp. 451 and 596; 3 pages.
[cited by applicant]
Barker, “Administration of N,N-dimethyltryptamine (DMT) in psychedelic therapeutics and research and the study of endogenous DMT.” Psychopharmacology (Berl). Jun. 2022; 239(6): 1749-1763. Epub Jan. 22, 2022, with erratu…
[cited by applicant]
Barker, “N, N-Dimethyltryptamine (DMT), an Endogenous Hallucinogen: Past, Present, and Future Research to Determine Its Role and Function.” Front Neurosci. Aug. 6, 2018:12:536. doi: 10.3389/fnins.2018.00536. eCollection…
[cited by applicant]
Barsuglia et al., “Intensity of mystical experiences occasioned by 5-MeO-DMT and comparison with a prior psilocybin study.” Front Psychol. Dec. 6, 2018: 9: 2459. doi: 10.3389/fpsyg.2018.02459. eCollection 2018. 6 pages.
[cited by applicant]
Benneyworth et al., “Complex discriminative stimulus properties of (+)lysergic acid diethylamide (LSD) in C57BI/6J mice.” Psychopharmacology (2005) 179, 854-862.
[cited by applicant]
Berge et al. “Pharmaceutical Salts” Jan. 1977, Journal of Pharmaceutical Sciences, 66(1):1-19.
[cited by applicant]
Bergin, “Preliminary X-ray crystallographic study of some psychoactive indole bases.” Acta Cryst. (1968). B24, 882, https://doi.org/10.1107/S0567740868003353, 1 page.
[cited by applicant]
Bergin, “The structure of the catecholamines. II. The crystal structure of dopamine hydrochloride.” Acta Crystallogr B Struct Crystallogr Cryst Chem. Nov. 15, 1968;24(11):1506-10. doi: 10.1107/s0567740868004553.
[cited by applicant]
Bibi et al., “Use of Permeapad® for prediction of buccal absorption: A comparison to in vitro, ex vivo and in vivo method.” Eur J Pharm Sci. Oct. 10, 2016:93:399-404. doi:10.1016/j.ejps.2016.08.041. Epub Aug. 24, 2016.
[cited by applicant]
Brandt et al., “Analytical methods for psychoactive N,N-dialkylated tryptamines.” Trends in Analytical Chemistry, vol. 29, No. 8, 2010, pp. 858-869.
[cited by applicant]
Brandt et al., “Characterization of the synthesis of N,N-dimethyltryptamine by reductive amination using gas chromatography ion trap mass spectrometry.” Drug Test Anal. Jul. 2010; 2(7): 330-8. doi: 10.1002/dta.142.
[cited by applicant]
Brito-Da-Costa, et al., “Toxicokinetics and toxicodynamics of ayahuasca alkaloids N, N-dimethyltryptamine (DMT), harmine, harmaline and tetrahydroharmine: clinical and forensic impact.” Pharmaceuticals (Basel). Oct. 23,…
[cited by applicant]
Buchwald, Peter, “Soft drugs: design principles, success stories, and future perspectives.” Expert Opin Drug Metab Toxicol. Aug. 2020; 16(8): 645-650. Epub Jun. 20, 2020.
[cited by applicant]
Bugaenko et al., “Synthesis of indoles: recent advances.” Russ. Chem. Rev., 2019, 88 (2)99-159, 62 pages.
[cited by applicant]
Cameron et al., “A non-hallucinogenic psychedelic analogue with therapeutic potential.” Nature. Jan. 2021;589(7842):474-479. doi: 10.1038/s41586-020-3008-z. Epub Dec. 9, 2020, and Reporting Summary, 24 pages.
[cited by applicant]
Cameron et al., “Chronic, Intermittent Microdoses of the Psychedelic N , N-Dimethyltryptamine (DMT) Produce Positive Effects on Mood and Anxiety in Rodents.” ACS Chemical Neuroscience, vol. 10, No. 7, Jul. 17, 2019 (Jul…
[cited by applicant]
Cameron et al., “Effects of N, N-Dimethyltryptamine on Rat Behaviors Relevant to Anxiety and Depression.” ACS Chem Neurosci, Jul. 18, 2018; 9(7): 1582-1590. Epub Apr. 24, 2018.
[cited by applicant]
Carhart-Harris et al., “The therapeutic potential of psychedelic drugs: past, present, and future.” Neuropsychopharmacology (2017); 42(11): 2105-2113. doi: 10.1038/npp.2017.84. Epub Apr. 26, 2017.
[cited by applicant]
Carhart-Harris, “Psilocybin for treatment-resistant depression: fMRI-measured brain mechanisms.” Sci Rep. Oct. 13, 2017; 7(1): 13187. doi: 10.1038/s41598-017-13282-7. 11 pages.
[cited by applicant]
Carter et al., “Modulating the rate and rhythmicity of perceptual rivalry alternations with the mixed 5-HT2A and 5-HT1A agonist psilocybin.” Neuropsychopharmacology (2005); 30(6): 1154-1162. doi: 10.1038/sj.npp.1300621.
[cited by applicant]
Carvalho et al., “Mucoadhesive drug delivery systems,” BJPS, vol. 46, n. 1, Jan./Mar., 2010. 18 pages.
[cited by applicant]
CAS Registry No. 1152718-19-8, Benzenemethanamine, N-[4-(1,1-dimethylethyl)cyclohexyl]-2,4-difluoro-α-methyl-, Jun. 5, 2009, 1 page.
[cited by applicant]
CAS Registry No. 1152826-22-6, Benzenemethanamine, 5-bromo-N-[4-(1,1-dimethylpropyl)cyclohexyl]-2-fluoro-, Jun. 7, 2009, 1 page.
[cited by applicant]
CAS Registry No. 1154138-59-6, Benzenemethanamine, N-[4-(1,1-dimethylpropyl)cyclohexyl]-2,5-difluoro-, Jun. 9, 2009, 1 page.
[cited by applicant]
CAS Registry No. 127456-43-3, Phenol, 2-[[[4-(1,1-dimethylethyl)cyclohexyl]amino]methyl]-4-(1, 1-dimethylpropyl)-, trans-(9CI), Jun. 1, 1990, 1 page.
[cited by applicant]
CAS Registry No. 127456-44-4, 1H-Inden-5-ol, 6-[[[4-(1,1-dimethylethyl)cyclohexyl]amino]methyl]-2,3-dihydro-, trans-(9CI), Jun. 1, 1990, 1 page.
[cited by applicant]
CAS Registry No. 127456-45-5, Phenol, 4-(1,1-dimethylethyl)-2-[[[4-(1,1-dimethylethyl)cyclohexyl]amino]methyl]-, trans-(9CI), Jun. 1, 1990, 1 page.
[cited by applicant]
CAS Registry No. 127456-46-6, Phenol, 4-(1, 1-dimethylethyl)-2-[[[4-(1, 1-dimethylethyl)cyclohexyl]amino]methyl]-6-methyl-, hydrochloride, trans-(9CI), Jun. 1, 1990, 1 page.
[cited by applicant]
CAS Registry No. 127456-52-4, Phenol, 2-[[[4-(1,1-dimethylethyl)cyclohexyl]amino]methyl]-4-(1-methylethyl)-, cis-(9CI), Jun. 1, 1990, 1 page.
[cited by applicant]
CAS Registry No. 127456-56-8, Phenol, 4-chloro-2-[[[4-(1,1-dimethylethyl)cyclohexyl]amino]methyl]-, trans-(9CI), Jun. 1, 1990, 1 page.
[cited by applicant]
CAS Registry No. 127456-57-9, Phenol, 2-[[[4-(1,1-dimethylethyl)cyclohexyl]amino]methyl]-4-fluoro-, trans-(9Cl), Jun. 1, 1990, 2 pages.
[cited by applicant]
CAS Registry No. 1308467-14-2, 1,2-Benzenediol, 3-[[[4-(1,1-dimethylpropyl)cyclohexyl]amino]methyl]-, Jun. 10, 2011, 1 page.
[cited by applicant]
CAS Registry No. 1405571-87-0, Benzenemethanamine, 2-bromo-N-[4-(1,1-dimethylpropyl)cyclohexyl]-5-fluoro-, Nov. 23, 2012, 1 page.
[cited by applicant]
CAS Registry No. 1406541-63-6, Phenol, 2-chloro-4-[[[4-(1,1-dimethylpropyl)cyclohexyl]amino]methyl]-, Nov. 25, 2012, 1 page.
[cited by applicant]
CAS Registry No. 1411655-23-6, Benzenemethanamine, N-[4-(1,1-dimethylpropyl)cyclohexyl]-2,3-difluoro-, Dec. 5, 2012, 1 page.
[cited by applicant]
CAS Registry No. 1456349-79-3, Benzenemethanamine, 2,3-dichloro-N-[4-(1,1-dimethylpropyl)cyclohexyl]-, Oct. 6, 2013, 1 page.
[cited by applicant]
CAS Registry No. 1458497-71-6, Benzenemethanamine, 2,4-dichloro-N-[4-(1,1-dimethylethyl)cyclohexyl]-α-methyl-, Oct. 15, 2013, 1 page.
[cited by applicant]
CAS Registry No. 1459328-13-2, Phenol, 2-bromo-4-[[[4-(1,1-dimethylpropyl)cyclohexyl]amino]methyl]-, Oct. 16, 2013, 1 page.
[cited by applicant]
CAS Registry No. 1490220-45-5, Benzenemethanamine, 2-bromo-5-chloro-N-[4-(1,1-dimethylpropyl)cyclohexyl]-, Dec. 8, 2013, 1 page.
[cited by applicant]
CAS Registry No. 1515984-46-9, Benzamide, N-(4-aminocyclohexyl)-3-chloro-N,5-dimethyl-, Jan. 10, 2014, 1 page.
[cited by applicant]
CAS Registry No. 1542027-51-9, Phenol, 3-chloro-2-[[[4-(1,1-dimethylpropyl)cyclohexyl]amino]methyl]-, Feb. 11, 2014, 1 page.
[cited by applicant]
CAS Registry No. 1624268-56-9, Benzamide, 4-[[[4-(1,1-dimethylethyl)cyclohexyl]amino]methyl]-N-methyl-, Sep. 22, 2014, 1 page.
[cited by applicant]
CAS Registry No. 1712122-27-4, Benzenemethanamine, 5-chloro-N-[4-(1,1-dimethylpropyl)cyclohexyl]-2-fluoro-, May 25, 2015, 1 page.
[cited by applicant]
CAS Registry No. 1772618-27-5, Phenol, 3-[[[4-(1,1-dimethylpropyl)cyclohexyl]amino]methyl]-5-fluoro-, Jun. 3, 2015, 1 page.
[cited by applicant]
CAS Registry No. 1775706-37-0, Phenol, 2-chloro-6-[[[4-(1,1-dimethylpropyl)cyclohexyl]amino]methyl]-, Jun. 8, 2015, 1 page.
[cited by applicant]
CAS Registry No. 1858436-76-6, Bicyclo[3.1.0]hexan-2-amine, N-[(3-chloro-5-methylphenyl)methyl]-, Feb. 3, 2016, 1 page.
[cited by applicant]
CAS Registry No. 1931388-10-1, Benzenemethanamine, 2,5-dichloro-N-[4-(1,1-dimethylpropyl)cyclohexyl]-, Jun. 14, 2016, 1 page.
[cited by applicant]
CAS Registry No. 1939264-55-7, Phenol, 4-[[[4-(1,1-dimethylpropyl)cyclohexyl]amino]methyl]-2-fluoro-, Jun. 26, 2016, 1 page.
[cited by applicant]
CAS Registry No. 1939792-99-0, Benzenemethanamine, 5-bromo-2-chloro-N-[4-(1,1-dimethylpropyl)cyclohexyl]-, Jun. 27, 2016, 1 page.
[cited by applicant]
CAS Registry No. 1962333-15-8, Benzenemethanamine, N-[4-(1,1-dimethylpropyl)cyclohexyl]-5-fluoro-2-methyl-, Jul. 29, 2016, 1 page.
[cited by applicant]
CAS Registry No. 2032268-58-7, Cyclohexanecarboxylic acid, 4-[[(3-chloro-5-methylphenyl)methyl]amino]-, Nov. 15, 2016, 1 page.
[cited by applicant]
CAS Registry No. 2199998-08-6, Cyclohexanecarboxylic acid, 2-[[(3-chloro-5-methylphenyl)methyl]amino]-1-methyl-, Mar. 27, 2018, 1 page.
[cited by applicant]
CAS Registry No. 2202151-69-5, Cyclohexanecarboxylic acid, 3-[[(3-chloro-5-methylphenyl)methyl]amino]-, Mar. 30, 2018, 1 page.
[cited by applicant]
CAS Registry No. 2322790-81-6, Benzenemethanamine, N-[4-(1,1-dimethylethyl)cyclohexyl]-3-(trifluoromethyl)-, Jun. 2, 2019, 1 page.
[cited by applicant]
CAS Registry No. 2419600-39-6, Benzenemethanamine, 3-chloro-N-[4-(1,1-dimethylpropyl)cyclohexyl]-5-methyl-, Jun. 5, 2020, 1 page.
[cited by applicant]
CAS Registry No. 415970-94-4, Benzenemethanamine, N-[4-(1,1-dimethylethyl)cyclohexyl]-3,5-dimethoxy-, May 15, 2002, 1 page.
[cited by applicant]
CAS Registry No. 744981-83-7, Phenol, 2,6-dibromo-4-[[[4-(1,1-dimethylethyl)cyclohexyl]amino]methyl]-, Sep. 15, 2004, 1 page.
[cited by applicant]
CAS Registry No. 793633-39-3, Phenol, 4-(1,1-dimethylethyl)-2-[[[trans-4-(1,1-dimethylethyl)cyclohexyl]amino]methyl]-6-methyl-, Dec. 6, 2004, 1 page.
[cited by applicant]
Cayman Chemical “Safety Data Sheet Acc. to OSHA HCS”, N,N-DMT (Succinate), CAS No. 2853570-32-6, Cayman Chemical: 1-7, Revised Feb. 15, 2024.
[cited by applicant]
Cayman Chemical, “Safety Data Sheet”, Caymanchem.com, Apr. 21, 2021, [online] available at: https://cdn.caymanchem.com/cdn/msds/33586m.pdf. 6 printed pages.
[cited by applicant]
Cayman Chemical, product information for Item No. 33586, “N,N-DMT (succinate).” Apr. 26, 2021, 1 page.
[cited by applicant]
Chadeayne, Andrew R et al., “The Crystal Structure of 4-AcO-DMT Fumarate.” Psychedelic Science Review, Science Review Team, Mar. 25, 2019, online at: https://psychedelicreview.com/the-crystal-structure-of-4-aco-dmt-fuma…
[cited by applicant]
Chegaev, et al., “NO-donor melatonin derivatives: synthesis and in vitro pharmacological characterization”, J Pineal Res. Apr. 2007; 42(4): 371-85.
[cited by applicant]
Chen, et al., “Structure-activity relationships in a series of 5-[(2, 5-dihydroxybenzyl) amino] salicylate inhibitors of EGF-receptor-associated tyrosine kinase: importance of additional hydrophobic aromatic interaction…
[cited by applicant]
ClinicalTrials.gov, “Effects of Dimethyltryptamine in Healthy Subjects (DMT)”, Apr. 20, 2020, 9 pages. Retrieved on Jun. 24, 2022 from https://clinicaltrials.gov/ct2/show/NCT04353024.
[cited by applicant]
Cocchi et al., “Novel Psychoactive Phenethylamines: Impact on Genetic Material.” Int J Mol Sci. Dec. 17, 2020; 21(24): 9616. doi: 10.3390/ijms21249616. 17 pages.
[cited by applicant]
Corne et al., “A possible correlation between drug-induced hallucinations in man and a behavioural response in mice”, Psychopharmacologia (Berl.) (1967); 11: 65-78. doi: 10.1007/BF00401509.
[cited by applicant]
Cozzi, Nicholas V. et al., “Synthesis and characterization of high-purity N,N-dimethyltryptamine hemifumarate for human clinical trials.” Drug Test Anal. Oct. 2020; 12(10): 1483-1493. doi: 10.1002/dta.2889. Epub Jul. 14…
[cited by applicant]
Daiber et al., “Organic Nitrate Therapy, Nitrate Tolerance, and Nitrate-Induced Endothelial Dysfunction: Emphasis on Redox Biology and Oxidative Stress.” Antioxid Redox Signal. Oct. 10, 2015;23(11):899-942.).
[cited by applicant]
Dakic et al., “Short term changes in the proteome of human cerebral organoids induced by 5-MeO-DMT.” Sci Rep. Oct. 9, 2017;7(1):12863. doi: 10.1038/s41598-017-12779-5. 13 pages.
[cited by applicant]
Dalgleish, T., et al., “Transdiagnostic Approaches to Mental Health Problems: Current Status and Future Directions.” Journal of Consulting and Clinical Psychology, 2020, vol. 88, No. 3, 179-195.
[cited by applicant]
Davis et al., “5-methoxy-N, N-dimethyltryptamine (5-MeO-DMT) used in a naturalistic group setting is associated with unintended improvements in depression and anxiety.” Am J Drug Alcohol Abuse. 2019; 45(2): 161-169. doi…
[cited by applicant]
Davis, et al., “The epidemiology of 5-methoxy-N, N-dimethyltryptamine (5-MeO-DMT) use: Benefits, consequences, patterns of use, subjective effects, and reasons for consumption.” J Psychopharmacol, Jul. 2018. vol. 2, Iss…
[cited by applicant]
De Barros et al., “Synthesis of 25X-BOMes and 25X-NBOHs (X = H, I, Br) for pharmacological studies and as reference standards for forensic purposes.” Tetrahedron Letters 66 (2021) 152804, 4 pages.
[cited by applicant]
Declaration of Majed Fawaz under 37 C.F.R. § 1.130, in U.S. Appl. No. 17/824,861, dated Jun. 2024, 2 pages.
[cited by applicant]
Dimoitou, “Nasal spray” #3 Posted : Jun. 27, 2014 6:58:57 pm DMT-Nexus, Jun. 27, 2014, https://forum.dmt-nexus.me/threads/nasal-spray.343226/. 5 pages.
[cited by applicant]
Du, M., “An Overview on Transmucosal Permeability and Formulation.” J Develop Drugs. 13:227, (2024), 2 pages.
[cited by applicant]
Dunlap et al., “Identification of psychoplastogenic N, N-dimethylaminoisotryptamine (isoDMT) analogues through structure-activity relationship studies.” J Med Chem Feb. 13, 2020; 63(3): 1142-1155. Epub Jan. 24, 2020. 14…
[cited by applicant]
Dunlap, Lee, E. et al., Reaction of N, N-Dimethyltryptamine with Dichloromethane Under Common Experimental Conditions, ACS Omega, 2018, 3, 4968-4973.
[cited by applicant]
Durham and Russo, “Regulation of calcitonin gene-related peptide secretion by a serotonergic antimigraine drug.” J Neurosci. May 1, 1999; 19(9): 3423-9. doi: 10.1523/JNEUROSCI.19-09-03423.1999.
[cited by applicant]
Extended European Search Report for EP Application No. 22796577.9, dated Mar. 10, 2025, 10 pages.
[cited by applicant]
Extended European Search Report for EP Application No. 22812068.9, dated Mar. 28, 2025, 13 pages.
[cited by applicant]
Falkenberg et al., “The crystal and molecular structure of (N,N)-dimethyltryptamine.” Acta Crystallogr., Sect B28, 3075-3083, Mar. 9, 1972, 9 pages.
[cited by applicant]
Gaujac et al. “Determination of N,N-dimethyltryptamine in beverages consumed in religious practices by headspace solid-phase microextraction followed by gas chromatography ion trap mass spectrometry,” Talanta. Mar. 15, …
[cited by applicant]
Gaujac et al., “Investigations into the polymorphic properties of N, N-dimethyltryptamine by X-ray diffraction and differential scanning calorimetry,” Microchemical Journal 110, Mar. 2, 2013, 12 pages.
[cited by applicant]
Glatfelter G, et al., “Synthesis, Structural Characterization, and Pharmacological Activity of Novel Quaternary Salts of 4-Substituted Tryptamines”, ACS Omega, Jul. 2022, vol. 7(28), pp. 24888-24894.
[cited by applicant]
Glennon et al., “Hallucinogens as discriminative stimuli: A comparison of 4-OMe and 5-OMe DMT with their methylthio counterparts”, Life Science, Pergamon Press, Oxford, GB, vol. 30, No. 5, Feb. 1, 1982 (Feb. 1, 1982), p…
[cited by applicant]
Glennon et al., “Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl-and indolylalkylamines.” J Med Chem. Jun. 24, 1994; 37(13): 1929-35. doi: 10.1021/jm00039a004.
[cited by applicant]
Glennon et al., “Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines”, J Med Chem. Jan. 1984; 27(1): 41-5.
[cited by applicant]
Gonzalez-Maeso et al., “Hallucinogens Recruit Specific Cortical 5-HT2A Receptor-Mediated Signaling Pathways to Affect Behavior,” Neuron, Feb. 2007, 53, 439-452.
[cited by applicant]
Gribble, “Recent developments in indole ring synthesis-methodology and applications”, Journal of the Chemical Society, Perkin Transactions, 2000, pp. 1045-1075.
[cited by applicant]
Griffiths et al., “Psilocybin produces substantial and sustained decreases in depression and anxiety in patients with life-threatening cancer: a randomized double-blind trial”, Journal of Psychopharmacology (2016); 30: …
[cited by applicant]
Grundke et al., “Photochemical α-Aminonitrile Synthesis Using Zn-Phthalocyanines as Near-Infrared Photocatalysts”, J Org Chem. May 6, 2022; 87(9): 5630-5642, with supporting info. Epub Apr. 14, 2022. 60 pages.
[cited by applicant]
Gurevich and Gurevich, “GPCR Signaling Regulation: The Role of GRKs and Arrestins”, Front Pharmacol. Feb. 19, 2019: 10: 125. eCollection 2019, 11 pages.
[cited by applicant]
Halberstadt, A. L., “Recent Advances in the Neuropsychopharmacology of Serotonergic Hallucinogens.” Behav Brain Res. Jan. 15, 2015: 277: 99-120. doi: 10.1016/j.bbr.2014.07.016. Epub Jul. 15, 2014.
[cited by applicant]
Halberstadt et al., “Differential contributions of serotonin receptors to the behavioral effects of indoleamine hallucinogens in mice”, J Psychopharmacol. Nov. 2011; 25(11): 1548-61. Epub Dec. 8, 2010.
[cited by applicant]
Hamada et al., “Water-soluble prodrugs of dipeptide HIV protease inhibitors based on O→N intramolecular acyl migration: Design, synthesis and kinetic study” Bioorg Med Chem. Jan. 2, 2004;12(1):159-70. doi: 10.1016/j.bmc…
[cited by applicant]
Hansen et al., “Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists.” Bioorganic & Medicinal Chemistry 23 (2015), 3933-3937.
[cited by applicant]
Hansen et al., “Synthesis and Structure-Activity Relationships of N-Benzyl Phenethylamines as 5-HT2A/2C Agonists.” ACS Chem Neurosci. Mar. 19, 2014;5(3):243-9. doi: 10.1021/cn400216u. Epub Jan. 15, 2014.
[cited by applicant]
Harriott et al., “Animal models of migraine and experimental techniques used to examine trigeminal sensory processing”, J Headache Pain. Aug. 29, 2019; 20(1): 91. 15 pages.
[cited by applicant]
Hart et al., “Melting Point Determination, Melting Range”, Adapted from Organic Chemistry: A Short course, 13th ed. Houghton-Mifflin, Boston, 2012, available at: https://chemistry.sites.clemson.edu/organic/Labs/2270Docs…
[cited by applicant]
Hasegawa et al., “A Novel Methodology for Preparing 5-chloro- and 5-bromo-tryptamines and tryptophans, and its Application to the Synthesis of (+/−)-bromochelonin BI.” (1999), Heterocycles, vol. 51, No. 12, pp. 2815-282…
[cited by applicant]
Holze et al. “Distinct acute effects of LSD, MDMA, and Damphetamine in healthy subjects.” Neuropsychopharmacology. Feb. 2020;45(3):462-471.
[cited by applicant]
Humphrey et al., “Practical methodologies for the synthesis of indoles”, Chem Rev. Jul. 2006; 106(7): 2875-911, 37 pages.
[cited by applicant]
Huttunen, et al., “Prodrugs-from Serendipity to Rational Design”, Pharmacological Reviews, vol. 63, No. 3, Sep. 2011, pp. 750-771.
[cited by applicant]
International Preliminary Report on Patentability for International Application No. PCT/US2022/026396, mailed Nov. 9, 2023, 8 pages.
[cited by applicant]
International Preliminary Report on Patentability for International Application No. PCT/US2022/030912, mailed Dec. 7, 2023, 10 pages.
[cited by applicant]
International Preliminary Report on Patentability for International Application No. PCT/US2022/032918, mailed Dec. 21, 2023, 7 pages.
[cited by applicant]
International Preliminary Report on Patentability for International Application No. PCT/US2022/045336, mailed Apr. 11, 2024, 7 pages.
[cited by applicant]
International Preliminary Report on Patentability for International Application No. PCT/US2022/047520, mailed May 10, 2024, 8 pages.
[cited by applicant]
International Preliminary Report on Patentability for International Application No. PCT/US2023/073574, mailed Mar. 20, 2025, 9 pages.
[cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2022/026396, mailed Jul. 28, 2022, 10 pages.
[cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2022/030912, mailed Oct. 5, 2022, 20 pages.
[cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2022/032918, mailed Oct. 12, 2022, 10 pages.
[cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2022/045336, mailed Jan. 13, 2023, 14 pages.
[cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2022/047520, mailed Mar. 1, 2023, 11 pages.
[cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2022/082465, mailed Jun. 6, 2023, 11 pages.
[cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2023/073574, mailed Feb. 16, 2024, 13 pages.
[cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2023/077879, mailed Apr. 4, 2024, 11 pages.
[cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2023/082080, mailed Apr. 4, 2024, 8 pages.
[cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2023/084319, mailed May 20, 2024, 13 pages.
[cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2024/026797, mailed Sep. 6, 2024, 10 pages.
[cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2024/036639, mailed Sep. 23, 2024, 11 pages.
[cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2024/038804, mailed Dec. 17, 2024, 14 pages.
[cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2024/039503, mailed Nov. 5, 2024, 17 pages.
[cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2024/045494, mailed Nov. 15, 2024, 11 pages.
[cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2024/049678, mailed Jan. 21, 2025, 9 pages.
[cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2025/014571, mailed Mar. 21, 2025, 15 pages.
[cited by applicant]
International Search Report and Written Opinion for PCT Application No. PCT/US2024/061478 mailed Apr. 23, 2025, 10 pages.
[cited by applicant]
Invitation to Pay Additional Fees for International Application No. PCT/US2022/030912, mailed Jul. 28, 2022, 8 pages.
[cited by applicant]
Invitation to Pay Additional Fees for International Application No. PCT/US2022/032918, mailed Aug. 12, 2022, 2 pages.
[cited by applicant]
Invitation to Pay Additional Fees for International Application No. PCT/US2022/082465, mailed Mar. 16, 2023, 3 pages.
[cited by applicant]
Invitation to Pay Additional Fees for International Application No. PCT/US2023/073574, mailed Nov. 6, 2023, 2 pages.
[cited by applicant]
Invitation to Pay Additional Fees for International Application No. PCT/US2024/026797, mailed Jun. 25, 2024, 2 pages.
[cited by applicant]
Invitation to Pay Additional Fees for International Application No. PCT/US2024/038804, mailed Sep. 23, 2024, 3 pages.
[cited by applicant]
Invitation to Pay Additional Fees for International Application No. PCT/US2024/039503, mailed Sep. 10, 2024, 2 pages.
[cited by applicant]
Invitation to Pay Additional Fees for International Application No. PCT/US2024/061478, mailed Feb. 25, 2025, 2 pages.
[cited by applicant]
Invitation to Pay Additional Fees for International Application No. PCT/US22/47520, mailed Jan. 3, 2023, 2 pages.
[cited by applicant]
Kaminska et al., “25C-NBOMe short characterization”, Forensic Toxicology, 2020, pp. 490-495.
[cited by applicant]
Klein et al., “Toward selective drug development for the human 5-hydroxytryptamine 1E receptor: a comparison of 5-hydroxytryptamine 1E and 1F receptor structure-affinity relationships”, J Pharmacol Exp Ther. Jun. 2011; …
[cited by applicant]
Kline et al, “Structure-activity relationships in potentially hallucinogenic N, N-dialkyltryptamines substituted in the benzene moiety.” J Med Chem. Aug. 1982; 25(8):908-13. doi: 10.1021/jm00350a005.
[cited by applicant]
Kraehenmann et al., “Dreamlike effects of LSD on waking imagery in humans depend on serotonin 2A receptor activation”, Psychopharmacology (Berl) (2017); 234: 2031-2046. doi: 10.1007/s00213-017-4610-0. Epub Apr. 7, 2017.
[cited by applicant]
Kraehenmann et al., “LSD Increases Primary Process Thinking via Serotonin 2A Receptor Activation”, Frontiers in Pharmacology (2017); 8: 814; 9 pages. doi: 10.3389/fphar.2017.00814.
[cited by applicant]
Krise, J. P., et al., “Novel prodrug approach for tertiary amines: synthesis and preliminary evaluation of N-phosphonooxymethyl prodrugs”, J Med Chem. Aug. 12, 1999; 42(16): 3094-100.
[cited by applicant]
Kucklander, et al., “Darstellung und Oxidation von 2-(2, 5-Dihydroxy-phenyl)-ethylamin-Derivaten, II/Synthesis and Oxidation of 2-(2, 5-Dihydroxyphenyl)-ethylamine Derivatives, II”, Zeitschrift für Naturforschung B, 198…
[cited by applicant]
Li et al., “Treatment of breast and lung cancer cells with a N-7 benzyl guanosine monophosphate tryptamine phosphoramidate pronucleotide (4Ei-1) results in chemosensitization to gemcitabine and induced elF4E proteasomal…
[cited by applicant]
Lima da Cruz et al., “Corrigendum: A Single Dose of 5-MeO-DMT Stimulates Cell Proliferation, Neuronal Survivability, Morphological and Functional Changes in Adult Mice Ventral Dentate Gyrus.” Front Mol Neurosci. Sep. 4,…
[cited by applicant]
Lyon et al., “3, 4-Methylenedioxymethamphetamine (MDMA): stereoselective interactions at brain 5-HT
[cited by applicant]
Madsen et al., “Psilocybin-induced reduction in chronic cluster headache attack frequency correlates with changes in hypothalamic functional connectivity”, medRxiv. Jul. 10, 2022: 2022-07.
[cited by applicant]
Madsen et al., “Psychedelic effects of psilocybin correlate with serotonin 2A receptor occupancy and plasma psilocin levels,” Neuropsychopharmacology (2019) 44: 1328-1334.
[cited by applicant]
Malaca, S., et al., “Toxicology and Analysis of Psychoactive Tryptamines.” Int J Mol Sci. Dec. 4, 2020; 21(23): 9279. doi: 10.3390/ijms21239279. 30 pages.
[cited by applicant]
McBride, “Bufotenine: Toward an Understanding of Possible Psychoactive Mechanisms”, Journal of Psychoactive Drugs, Jul.-Sep. 2000, pp. 321-331.
[cited by applicant]
McClure-Begley and Roth, “The promises and perils of psychedelic pharmacology for psychiatry”, Nat Rev Drug Discov. Jun. 2022; 21(6): 463-473. Epub Mar. 17, 2022.
[cited by applicant]
Mertens and Preller, “Classical Psychedelics as Therapeutics in Psychiatry—Current Clinical Evidence and Potential Therapeutic Mechanisms in Substance Use and Mood Disorders”, Pharmacopsychiatry. Jul. 2021; 54(4): 176-1…
[cited by applicant]
Milne et al., “Metabolic engineering of
[cited by applicant]
Mithoefer et al., “The safety and efficacy of {+/−}3,4-methylenedioxymethamphetamine-assisted psychotherapy in subjects with chronic, treatment-resistant posttraumatic stress disorder: the first randomized controlled pi…
[cited by applicant]
Mokler D J et al: “The 5HT″2 antagonist pirenperone reverses disruption of FR-40 by hallucinogenic drugs.” Pharmacology Biochemistry and Behavior, Elsevier, US, vol. 22, No. 5, May 1, 1985 (May 1, 1985), pp. 677-682, XP…
[cited by applicant]
National Center for Biotechnology Information (2023). PubChem Substance Record for SID 309311543, SID 309311543, Source: Aurora Fine Chemicals LLC. Modified Jan. 30, 2016, retrieved from https://pubchem.ncbi.nlm.nih.gov…
[cited by applicant]
National Center for Biotechnology Information. PubChem Compound Summary for CID 15274381, 2-(7-Bromo-1H-indol-3-yl)ethan-1-amine. https://pubchem.ncbi.nlm.nih.gov/compound/2-_7-Bromo-1H-indol-3-yl_ethan-1-amine, Create …
[cited by applicant]
National Center for Biotechnology Information. PubChem Compound Summary for CID 156821129, [3-[2-(Dimethylamino)ethyl]-4-hydroxyindol-1-yl]methylphosphonic acid. https://pubchem.ncbi.nlm.nih.gov/compound/156821129, crea…
[cited by applicant]
National Center for Biotechnology Information. PubChem Compound Summary for CID 6089, Dimethyltryptamine. https://pubchem.ncbi.nlm.nih.gov/compound/Dimethyltryptamine. Create date: Mar. 26, 2005 (Mar. 26, 2005), 6 pages.
[cited by applicant]
National Center for Biotechnology Information. PubChem Compound Summary for CID 10624, Psilocybin. https://pubchem.ncbi.nlm.nih.gov/compound/Psilocybin. Create date Mar. 3, 2005, Accessed May 5, 2025. 62 pages.
[cited by applicant]
National Center for Biotechnology Information. PubChem Compound Summary for CID 88309097, [1-[[2-(1H-indol-3-yl)-1-(2-methylphenyl)ethyl]amino]-2-oxoethyl] carbamate. https://pubchem.ncbi.nlm.nih.gov/compound/88309097, …
[cited by applicant]
National Center for Biotechnology Information. PubChem Substance Record for SID 310331158, SID 310331158, Source: Aurora Fine Chemicals LLC. https://pubchem.ncbi.nlm.nih.gov/substance/310331158, Modify Date: Feb. 15, 20…
[cited by applicant]
National Center for Biotechnology Information. PubChem Substance Record for SID 369863280, SID 369863280, Source: Ambinter. https://pubchem.ncbi.nlm.nih.gov/substance/369863280. Deposit date May 25, 2018, Modify Date: M…
[cited by applicant]
National Center for Biotechnology Information. PubChem Substance Record for SID 433987242, N,N-dimethyltryptamine, Source: BioCyc. https://pubchem.ncbi.nlm.nih.gov/substance/433987242, Available Date: Sep. 28, 2020 [ret…
[cited by applicant]
National Center for Biotechnology Information. PubChem Substance Record for SID 627609, 2-(1H-indol-3-yl)ethanamine, Source: NIAID ChemDB. https://pubchem.ncbi.nlm.nih.gov/substance/627609, Modify Date: Jan. 21, 2015 [r…
[cited by applicant]
Nichols, D. E., “Psychedelics.” Pharmacol Rev. Apr. 2016;68(2):264-355.
[cited by applicant]
Nichols, “Hallucinogens.” Pharmacol Ther. Feb. 2004; 101(2):131-81.
[cited by applicant]
Nichols, “Structure-Activity Relationships of Phenethylamine Hallucinogens.” J Pharm Sci. Aug. 1981; 70(8): 839-49.
[cited by applicant]
Oliver et al., “Beta-blockers: Historical Perspective and Mechanisms of Action.” Rev Esp Cardiol (Engl Ed). Oct. 2019; 72(10): 853-862).
[cited by applicant]
Olson, David E., “The Subjective Effects of Psychedelics May Not Be Necessary for Their Enduring Therapeutic Effects”, ACS Pharmacol Transl Sci. Apr. 9, 2021; 4(2): 563-567. Published online Dec. 10, 2020.
[cited by applicant]
Ott, J., “Pharmañopo—Psychonautics: Human intranasal, sublingual, intrarectal, pulmonary and oral pharmacology of bufotenine.” J Psychoactive Drugs. Jul.-Sep. 2001; 33(3): 273-81.
[cited by applicant]
Ott, J., “Pharmepena-psychonautics: human intranasal, sublingual and oral pharmacology of 5-methoxy-N, N-dimethyl-tryptamine.” J Psychoactive Drugs. Oct.-Dec. 2001;33(4):403-7.
[cited by applicant]
Pandy-Szekeres et al., “GPCRdb in 2023: state-specific structure models using AlphaFold2 and new ligand resources”, Nucleic Acids Res. Jan. 6, 2023; 51(D1): D395-D402. 8 pages.
[cited by applicant]
Pandy-Szekeres et al., “The G Protein Database, GproteinDb.” Nucleic Acids Res. Jan. 7, 2022; 50(D1): D518-D525.
[cited by applicant]
Perez Custodio et al., “25B-NBOMe, a novel N-2-methoxybenzyl-phenethylamine (NBOMe) derivative, may induce rewarding and reinforcing effects via a dopaminergic mechanism: evidence of abuse potential.” Addict Biol. Nov. …
[cited by applicant]
Pokorny et al., “Modulatory effect of the 5-HT1A agonist buspirone and the mixed non-hallucinogenic 5-HT1A/2A agonist ergotamine on psilocybin-induced psychedelic experience.” Eur Neuropsychopharmacol. Apr. 2016; 26(4):…
[cited by applicant]
Pottie et al., “Identification of psychedelic new psychoactive substances (NPS) showing biased agonism at the 5-HT2AR through simultaneous use of β-arrestin 2 and miniGαq bioassays”, Biochem Pharmacol. Dec. 2020: 182: 1…
[cited by applicant]
Preller et al., “Effects of serotonin 2A/1A receptor stimulation on social exclusion processing,” PNAS, May 3, 2016, vol. 113, No. 18, 5119-5124.
[cited by applicant]
Preller et al., “Role of the 5-HT2A Receptor in Self- and Other-Initiated Social Interaction in Lysergic Acid Diethylamide-Induced States: A Pharmacological fMRI Study”, Journal of Neuroscience (Apr. 2018); 38(14): 3603…
[cited by applicant]
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