5-Methylpsilocybin

5-Methylpsilocybin is a psychedelic drug, a synthetic analogue of psilocybin, which has high serotonergic activity. It produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.

5-Methylpsilocybin

Clinical data
Other names	5-Methyl-4-phosphoryloxy-N,N-dimethyltryptamine; 5-Me-4-PO-DMT
Drug class	Serotonergic psychedelic; Hallucinogen; Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist
ATC code	None
Legal status
Legal status	Generally not controlled
Identifiers
IUPAC name 3-[2-(dimethylamino)ethyl]-5-methyl-1H-indol-4-yl dihydrogen phosphate
PubChem CID	170690552
ChemSpider	129466028
ChEMBL	ChEMBL5280975
Chemical and physical data
Formula	C13H19N2O4P
Molar mass	298.279 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=C(C2=C(C=C1)NC=C2CCN(C)C)OP(=O)(O)O
InChI InChI=1S/C13H19N2O4P/c1-9-4-5-11-12(13(9)19-20(16,17)18)10(8-14-11)6-7-15(2)3/h4-5,8,14H,6-7H2,1-3H3,(H2,16,17,18) Key:YEFXMKVFABOOBT-UHFFFAOYSA-N

Chemistry

Synthesis

5-Methylpsilocybin can be synthesized by enzymatic phosphorylation of its synthetic precursor, 5-methylpsilocin, using the enzyme 4-hydroxytryptamine kinase purified from Psilocybe cubensis.

See also

• Substituted tryptamine
• 5-Methoxypsilocybin

External links

• 5-Methylpsilocybin - Isomer Design