IP Library › Granted Patent US 12,454,515
Granted Patent B2
US 12,454,515 · App. 18/106,273 · Granted Oct 28, 2025

2-aminoindane compounds for mental disorders or enhancement

Inventor: Matthew Baggott (Redwood City, CA)
Assignee: Tactogen Inc
C07D307/79
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Quick Facts
Patent No.
US 12,454,515
App. No.
18/106,273
Granted
Oct 28, 2025
Kind
B2
Abstract

The present invention discloses 2-aminoindane Formulas I and II and their pharmaceutically acceptable salts, compositions and methods of use to modulate central nervous system activity, and to treat central nervous system disorders, such as post-traumatic stress, depression, anxiety, and adjustment disorders. In certain embodiments, the compounds of the present invention can be used for entactogenic therapy in counseling sessions, as needed periodically or consistently as necessary or desired.

Claims (66)

1. A compound of formula:

or a pharmaceutically acceptable salt or salt mixture thereof;

wherein:

R 1 is hydrogen, methyl, —CH 2 F, —CF 3 , ethyl, —CH 2 CH 2 F, —CH 2 CF 2 H, —CH 2 CF 3 , or —CF 2 CF 3 .

2. The compound of claim 1 wherein the compound is of formula:

or a pharmaceutically acceptable salt or salt mixture thereof.

3. The compound of claim 1 wherein the compound is of formula:

or a pharmaceutically acceptable salt or salt mixture thereof.

4. The compound of claim 1 wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

5. The compound of claim 4 wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

6. The compound of claim 4 wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

7. The compound of claim 4 wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

8. The compound of claim 5 wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

9. The compound of claim 6 wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

10. The compound of claim 7 wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

11. The compound of claim 5 wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

12. The compound of claim 6 wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

13. The compound of claim 7 wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

14. The compound of claim 4 wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

15. The compound of claim 4 wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

16. The compound of claim 4 wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

17. The compound of claim 14 wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

18. The compound of claim 15 wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

19. The compound of claim 16 wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

20. The compound of claim 14 wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

21. The compound of claim 15 wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

22. The compound of claim 16 wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

23. The compound of claim 1 , wherein the pharmaceutically acceptable salt(s) is hydrochloric acid, sulfate, aspartate, saccharate, phosphate, oxalate, acetate, amino acid anion, gluconate, maleate, malate, citrate, mesylate, nitrate or tartrate, or a mixture thereof.

24. A pharmaceutical composition comprising a compound of claim 1 or a pharmaceutically acceptable salt or salt mixture thereof and a pharmaceutically acceptable carrier or excipient.

25. The pharmaceutical composition of claim 24 , wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

26. The pharmaceutical composition of claim 25 , wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

27. The pharmaceutical composition of claim 25 , wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

28. The pharmaceutical composition of claim 25 , wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

29. The pharmaceutical composition of claim 25 , wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

30. The pharmaceutical composition of claim 25 , wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

31. The pharmaceutical composition of claim 25 , wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

32. The pharmaceutical composition of claim 25 , wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

33. The pharmaceutical composition of claim 25 , wherein the compound is:

or a pharmaceutically acceptable salt or salt mixture thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 24, 2025
From: BAGGOTT, MATTHEW
To: TACTOGEN INC
Reel/Frame 071821/0657 →
Continuity (3)
Continuation PCTUS2021045027 · Aug 6, 2021
Provisional Application 63062437 · Aug 6, 2020
Related Publication 20230183199A1 · Jun 15, 2023
References Cited (73)
US 5462965A · Roba et al. · 1995 [cited by applicant]
US 5639778A · Anderson et al. · 1997 [cited by applicant]
US 5708018A · Haadsma-Svensson et al. · 1998 [cited by applicant]
US 6291494B1 · Wikstrom et al. · 2001 [cited by applicant]
US 6423870B1 · Langlois et al. · 2002 [cited by applicant]
US 7045545B1 · Briner et al. · 2006 [cited by applicant]
US 7368477B2 · Gross et al. · 2008 [cited by applicant]
US 7396857B2 · Jandura et al. · 2008 [cited by applicant]
US 10137096B2 · Golan · 2018 [cited by applicant]
US 10406123B2 · Golan · 2019 [cited by applicant]
US 11767305B2 · Baggott · 2023 [cited by applicant]
US 20080200541A1 · Gross et al. · 2008 [cited by applicant]
US 20190054042A1 · Golan · 2019 [cited by applicant]
US 20200000747A1 · Golan · 2020 [cited by applicant]
US 20220096429A1 · Liechti · 2022 [cited by applicant]
US 20230159487A1 · Baggott · 2023 [cited by applicant]
US 20230257347A1 · Baggott · 2023 [cited by applicant]
US 20240083864A1 · Baggott · 2024 [cited by applicant]
FR 2717175A1 · 1995 [cited by examiner]
WO WO1994021608A1 · 1994 [cited by applicant]
WO WO2002072549A1 · 2002 [cited by applicant]
WO WO2008151170A2 · 2008 [cited by examiner]
WO WO2009117097A1 · 2009 [cited by applicant]
WO WO2021173273A1 · 2021 [cited by applicant]
WO WO2021257169A1 · 2021 [cited by applicant]
WO WO2022031566A1 · 2022 [cited by applicant]
WO WO2022106947A1 · 2022 [cited by applicant]
WO WO2022109050A1 · 2022 [cited by applicant]
WO WO2022120289A1 · 2022 [cited by applicant]
WO WO2022238507A1 · 2022 [cited by applicant]
U.S. Appl. No. 18/653,750, filed May 2, 2024, Baggott. [cited by applicant]
Baggott, Matthew J. et al. Effects of 3,4-methylenedioxymethamphetamine on socioemotional feelings, authenticity, and autobiographical disclosure in healthy volunteers in a controlled setting. J Psychopharmacol., 30(4):… [cited by applicant]
Barnett, Gene, et al. Quantitative structure activity relationships of analgesics, narcotic antagonists, and hallucinogens, National Institute on Drug Abuse, Research 22 Monograph Series, Apr. 20-22, 1978. [cited by applicant]
Brandt, Simon D et al. Chapter 11—Aminoindane Analogues. Novel Psychoactive Substances. Academic Press, pp. 261-283, Aug. 12, 2013. [cited by applicant]
Carleton, R. Nicholas et al. Brief Fear of Negative Evaluation Scale—Revised, Depression and Anxiety 23:297-303, May 10, 2006. [cited by applicant]
Clinicaltrials.gov. A Multi-Site Phase 3 Study of MDMA-assisted Psycholtherapy for PTSD (MAPP1)-NCT03537014. May 25, 2018. [cited by applicant]
De Brouwer, Geoffrey et al. A critical inquiry into marble-burying as a preclinical screening paradigm of relevance for anxiety and obsessive-compulsive disorder: Mapping the way forward, Cognitive, Affective, & Behavio… [cited by applicant]
Eshleman, A.J. et al. Structure-activity relationships of bath salt components: substituted cathinones and benzofurans at biogenic amine transporters. Psychopharmacology (Berl). Mar. 2019, 236(3):939-952. Published onli… [cited by applicant]
Feduccia, Allison A. et al. Breakthrough for Trauma Treatment: Safety and Efficacy of MDMA-Assisted Psychotherapy Compared to Paroxetine and Sertraline. Frontiers Psychiatry, 10:650, Sep. 12, 2019. [cited by applicant]
Fuwa, T. et al. Novel psychoactive benzofurans strongly increase extracellular serotonin level in mouse corpus striatum. J Toxicol Sci, 41(3):329-37. Published online: May 17, 2016. [cited by applicant]
Gallagher, C.T. et al. 5,6-Methylenedioxy-2-aminoindane: from laboratory curiosity to ‘legal high’. Hum Psychopharmacol., 27(2):106-12, Mar. 5, 2012. [cited by applicant]
Halberstadt, A.L. et al. 2-Aminoindan and its ring-substituted derivatives interact with plasma membrane monoamine transporters and a2-adrenergic receptors. Psychopharmacology (Berl), 236(3):989-999, Mar. 23, 2019. [cited by applicant]
Heifets, Boris D. et al. Distinct neural mechanisms for the prosocial and rewarding properties of MDMA, Science Translational Medicine, Research Article, Dec. 11, 2019. [cited by applicant]
Hysek, Cedric M. et al. MDMA enhances emotional empathy and prosocial behavior. Soc Cogn Affect Neurosci., Nov. 2014, 9(11):1645-52 (published Oct. 28, 2013). [cited by applicant]
Ilic, Marija et al. Cell-Based Radiotracer Binding and Uptake Inhibition Assays: A Comparison of In Vitro Methods to Assess the Potency of Drugs That Target Monoamine Transporters, Frontiers in Pharmacology, vol. 11, Ar… [cited by applicant]
International Search Report and Written Opinion for PCT/US21/45027, 9 pages, dated Nov. 17, 2021. [cited by applicant]
Iovino, Michele et al. Vasopressin secretion control: central neural pathways, neurotransmitters and effects of drugs. Curr Pharm Des., 18(30):4714-24, Jan. 1, 2012. [cited by applicant]
Joyce, B. Matthew et al. Adderall produces increased striatal dopamine release and a prolonged time course compared to amphetamine isomers, Psychophamacology, 2007, 191:669-677, (published online: Oct. 10, 2006). [cited by applicant]
Kim, M. et al. Effects of aromatic ring-substituted phenethylamines on the release of dopamine and serotonin. Forensic Toxicol., 37: 104-112, Sep. 6, 2018. [cited by applicant]
Luethi D, Liechti ME. Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics. Int J Neuropsychopharmacol. 21(10):926-93, Oct. 1, 2… [cited by applicant]
Luethi D, Liechti ME. Designer drugs: mechanism of action and adverse effects. Arch Toxicol. Apr. 2020;94(4):1085-1133. Published online: Apr. 6, 2020. [cited by applicant]
Ly, Calvin et al. Psychedelics Promote Structural and Functional Neural Plasticity. Cell Reports, 23 (11): 3170-3182, Jun. 12, 2018. [cited by applicant]
Masand, P. et al. Selective serotonin-reuptake inhibitors: an update. Harv Rev Psychiatry., 7(2): 69-84, Jul.-Aug. 1999. [cited by applicant]
Nenajdenko, Valentine G. et al. A new convenient approach to chiral β-aryl) heteroaryl)alkylamines, Tetrahedron: Assymmetry 12; 2517-2527, Oct. 15, 2001. [cited by applicant]
Nichols, D.E. et al. Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA). J Med Chem., 33(2):703-710, Feb. 1, 1990. [cited by applicant]
Olson, David E. Psychoplastogens: A promising class of plasticity-promoting neurotherapeutics, Journal of Experimental Neuroscience vol. 12: 1-4, Sep. 19, 2018. [cited by applicant]
Pacifici, Roberta et al. Paroxetine inhibits acute effects of 3,4-methylenedioxymethamphetamine on the immune system in humans, The Journal of Pharmacology and Experimental Therapeutics, Apr. 2004, vol. 309, No. 1, 285-… [cited by applicant]
Pitts, Elizabeth G. et al. (+)-MDMA and its enantiomers: potential therapeutic advantages of R(−)-MDMA. Psychopharmacology (Berl)., 235(2):377-392, Feb. 2018. [cited by applicant]
Pool, Eva et al. Measuring wanting and liking from animals to humans: A systematic review, Neuroscience and Biobehavioral Reviews, 124-142, Feb. 3, 2016. [cited by applicant]
Poos, George I. et al. Chapter 5, Anorexigenic Agents, Annual Reports in Medicinal Chemistry, Academic Press, 2:44-47, 1967. [cited by applicant]
Preller, K.H. et al. Modulation of Social Cognition via Hallucinogens and “Entactogens”. Front Psychiatry, 10:881, Dec. 3, 2019. [cited by applicant]
Ramos, Linnet et al. Acute Prosocial Effects of Oxytocin and Vasopressin When Given Alone or in Combination with 3,4-Methylenedioxymethamphetamine in Rats: Involvement of the V1A Receptor, Neuropsychopharmacology 38, 22… [cited by applicant]
Ray, T.S., Psychedelics and the human receptorome. PLOS One, 5(2):e9019, Feb. 2, 2010. [cited by applicant]
Sahai, M.A. et al. Combined in vitro and in silico approaches to the assessment of stimulant properties of novel psychoactive substances—The case of the benzofuran 5-MAPB. Progress in Neuro psychopharmacology & Biologic… [cited by applicant]
Sessa, Ben et al. A Review of 3,4-methylenedioxymethamphetamine (MDMA)-Assisted Psychotherapy. Front in Psychiatry; 10:138, Mar. 20, 2019. [cited by applicant]
Shimshoni, J.A. et al. Neurochemical binding profiles of novel indole and benzofuran MDMA analogues. Naunyn-Schmiedeberg's Arch Pharmacol 2017, 390, 15-24. Published: Sep. 20, 2016. [cited by applicant]
Spitzer, Manfred et al. Enantio-selective cognitive and brain activation effects of N-ethyl-3,4-methylenedioxyamphetamine in humans. Neuropharmacology. Aug. 2001; 41(2):263-71. Published online: Jul. 31, 2001. [cited by applicant]
Studerus, Erich et al. Prediction of psilocybin response in healthy volunteers, PLos One, vol. 7, Issue 2, Feb. 2012. [cited by applicant]
Studerus, Erich et al. Acute, subacute and long-term subjective effects of psilocybin in healthy humans: A pooled analysis of experimental studies, Journal of Psychopharmacology, Nov. 2011, vol. 25, Issue 11, 1434-1452.… [cited by applicant]
Tatsumi, Masahiko et al. Pharmacological profile of neuroleptics at human monoamine transporters, European Journal of Pharmacology 368. 277-283, Mar. 5, 1999. [cited by applicant]
Vallejos, Gabriel, Heteroarylisopropylamines as MAO inhibitors, Bioorganic & Medicinal Chemistry, 4450-4457, Jul. 15, 2005. [cited by applicant]
Vollenweider, Franz X. et al. Psychological and cardiovascular effects and short-term sequelae of MDMA (“ecstasy”) in MDMA-naïve healthy volunteers. Neuropsychopharmacology, 19(4):241-51, Oct. 1998. [cited by applicant]
Wee, Sunmee et al. Relationship between the serotonergic activity and reinforcing effects of a series of amphetamine analogs. J Pharmacol Exp Ther., 313(2):848-54. (published online: Jan. 26, 2005). [cited by applicant]