4-Hydroxy-5-methoxydimethyltryptamine
Identifiers | |
---|---|
| |
CAS Number |
|
ChemSpider |
|
UNII |
|
Chemical and physical data | |
Formula | C13H18N2O2 |
Molar mass | 234.299 g·mol−1 |
3D model (JSmol) |
|
Melting point | 146 to 147 °C (295 to 297 °F) (from ethyl acetate[1]) |
| |
InChI
| |
NY (what is this?) (verify) |
4-Hydroxy-5-methoxydimethyltryptamine, also known as 4-HO-5-MeO-DMT or psilomethoxin, is a hypothetical novel psychedelic drug.
It is structurally similar to other psychedelic tryptamines, but very little is known about its effects. The only report of it in the chemical literature was a paper published by Marc Julia's group at the Pasteur Institute in 1965.[1] This paper reports a 10 step synthesis of 4-HO-5-MeO-DMT from ortho-vanillin. Alexander Shulgin hypothesized that 4-HO-5-MeO-DMT could be biosynthesized by feeding Psilocybe cultures with 5-MeO-DMT, referencing a 1988 study by Jochen Gartz where transformation of DET into 4-HO-DET and 4-PO-DET was reported using such a method, with neither compounds having ever been found in nature.[2][3]
References
- ^ a b Julia M, Manoury P, Voillaume MC (1965). "No 209 - Recherches en série indolique. XIV (*) - Sur des méthoxy-5 hydroxy-4, méthoxy-5 hydroxy-6 et méthoxy-7 hydroxy-6 tryptamines". Bulletin de la Société Chimique de France (in French): 1417–1423.
- ^ "4-Hydroxy-5-methoxy-N,N-dimethyltryptamine, Psilocybe mushrooms, Psilocin". Ask Dr. Shulgin Online. Retrieved 2023-04-29.
- ^ Gartz J (1989). "Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe". Journal of Basic Microbiology. 29 (6): 347–352. doi:10.1002/jobm.3620290608. PMID 2614674. S2CID 43308695.
- v
- t
- e
(5-HT2A
agonists)
Benzofurans | |||||||||||||||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Lyserg‐ amides |
| ||||||||||||||||||||||||||||||||||||||||
Phenethyl‐ amines |
| ||||||||||||||||||||||||||||||||||||||||
Piperazines | |||||||||||||||||||||||||||||||||||||||||
Tryptamines |
| ||||||||||||||||||||||||||||||||||||||||
Others |
|
(NMDAR
antagonists)
Arylcyclo‐ hexylamines |
| ||||||
---|---|---|---|---|---|---|---|
Adamantanes | |||||||
Diarylethylamines | |||||||
Morphinans | |||||||
Others |
(mAChR
antagonists)
- Atropine
- Benactyzine
- Benzatropine
- Benzydamine
- Biperiden
- BRN-1484501
- Brompheniramine
- BZ
- CAR-226,086
- CAR-301,060
- CAR-302,196
- CAR-302,282
- CAR-302,368
- CAR-302,537
- CAR-302,668
- Chloropyramine
- Chlorphenamine
- Clemastine
- CS-27349
- Cyclizine
- Cyproheptadine
- Dicycloverine
- Dimenhydrinate
- Diphenhydramine
- Ditran
- Doxylamine
- EA-3167
- EA-3443
- EA-3580
- EA-3834
- Flavoxate
- Hyoscyamine
- JB-318
- JB-336
- Meclozine
- Mepyramine
- Orphenadrine
- Oxybutynin
- Pheniramine
- Phenyltoloxamine
- Procyclidine
- Promethazine
- Scopolamine
- Tolterodine
- Trihexyphenidyl
- Tripelennamine
- Triprolidine
- WIN-2299