Granted Patent B2

US 12,612,363 · App. 17/620,854 · Granted Apr 28, 2026

Inventors: Leonard Gerard Francis Patrick (Northumberland, GB); Shaun Neil Robinson (Northumberland, GB); Theis Terwey (Berlin, DE)

Assignee: GH RESEARCH IRELAND LIMITED

C07D209/16C07B2200/13

Abstract

Claims (35)

1 . A method of purifying 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) comprising:

dissolving crude 5-MeO-DMT in a recrystallisation solvent at a temperature above room temperature to obtain a solution;

cooling the obtained solution to a temperature below room temperature to precipitate a solid, the solid comprising crystalline 5-MeO-DMT;

separating the crystalline 5-MeO-DMT from the remaining solution; and

removing the recrystallisation solvent from the crystalline 5-MeO-DMT to obtain a purified 5-MeO-DMT product;

wherein the recrystallisation solvent contains at least 98 wt % methyl tert.-butyl ether (MTBE).

2 . The method according to claim 1 , wherein the recrystallisation solvent contains less than 2 wt % aliphatic hydrocarbons.

3 . The method according to claim 2 , wherein the recrystallisation solvent contains less than 1 wt % aliphatic hydrocarbons.

4 . The method according to claim 1 , wherein the recrystallisation solvent comprises less than 2 wt % in total of any anti-solvents, wherein an anti-solvent is a liquid in which a solubility of 5-MeO-DMT at any temperature occurring during the recrystallisation is less than 20% of the solubility in the recrystallisation solvent used to dissolve the crude 5-MeO-DMT.

5 . The method according to claim 4 , wherein the recrystallisation solvent contains less than 1 wt % of anti-solvents.

6 . The method according to claim 1 , wherein the obtained solution is cooled to a temperature of 0 to 20° C.

7 . The method according to claim 6 , wherein the temperature is 7 to 12° C.

8 . The method according to claim 1 , wherein the purifying of the crude 5-MeO-DMT to form the purified 5-MeO-DMT product results in

a total amount of impurities being reduced to below 0.5 area % as determined by HPLC using UV detection at 227 nm, and/or

an amount of each individual impurity being reduced to below 0.1 area % as determined by HPLC using UV detection at 227 nm.

9 . The method according to claim 8 , wherein the HPLC is carried out with an octadecyl carbon chain-bonded silica (C18) column and a mixed solvent based on 0.013M ammonium acetate in water and acetonitrile as eluent.

10 . The method according to claim 1 , wherein an amount of residual solvent in the purified 5-MeO-DMT product is not more than 5000 ppm.

11 . A method of purifying 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) comprising:

dissolving crude 5-MeO-DMT in a recrystallisation solvent at a temperature above room temperature to form a mother liquor, wherein the crude 5-MeO-DMT contains a total amount of impurities of 0.5 area % to 5 area %, based on peak area in an HPLC chromatogram;

cooling the mother liquor to a temperature below room temperature to precipitate a solid, the solid comprising crystalline 5-MeO-DMT;

separating the crystalline 5-MeO-DMT from the mother liquor; and

after the separation of the crystalline 5-MeO-DMT from the mother liquor, removing any remaining recrystallisation solvent from the crystalline 5-MeO-DMT to obtain a crystalline 5-MeO-DMT product in which the total amount of impurities in the crystalline 5-MeO-DMT product is below 0.5 area % and the amount of each individual impurity is below 0.1 area %;

wherein

the recrystallisation solvent contains at least 98 wt % methyl tert.-butyl ether (MTBE), and

the crystalline 5-MeO-DMT product is generated from the crude 5-MeO-DMT without performing column chromatography.

12 . The method according to claim 11 , wherein the 5-MeO-DMT is purified without adding a hydrocarbon as an anti-solvent.

13 . The method according to claim 11 , wherein the 5-MeO-DMT of the crude 5-MeO-DMT is in a free base form.

14 . The method according to claim 11 , wherein the crystalline 5-MeO-DMT product is generated from the crude 5-MeO-DMT without performing a distillation of 5-MeO-DMT.

15 . A method of purifying 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) comprising:

dissolving crude 5-MeO-DMT in a recrystallisation solvent at a temperature above room temperature to obtain a solution;

performing a recrystallization by cooling the obtained solution to a temperature below room temperature to precipitate a solid, the solid comprising crystalline 5-MeO-DMT;

separating the crystalline 5-MeO-DMT from the remaining solution; and

removing the recrystallisation solvent from the crystalline 5-MeO-DMT to obtain a purified 5-MeO-DMT product in which an amount of each individual impurity in the purified 5-MeO-DMT product is below 0.1 area %, the amount of each individual impurity being determined by HPLC carried out with an octadecyl carbon chain-bonded silica (C18) column and a mixed solvent based on 0.013M ammonium acetate in water and acetonitrile as eluent, using UV detection at 227 nm; wherein

the recrystallisation solvent contains at least 98 wt % methyl tert.-butyl ether (MTBE), and

the purified 5-MeO-DMT product is obtained by performing the recrystallization only once.

Assignments (2)

Priority Claims (1)

Continuity (1)

References Cited (400)