N-Acetylmescaline

Pharmaceutical compound From Wikipedia, the free encyclopedia

N-Acetylmescaline, also known as mescaline acetamide or as N-acetyl-3,4,5-trimethoxyphenethylamine, is a mescaline derivative found in trace quantities in peyote (Lophophora williamsii).^[1]^[2]^[3] It is a minor metabolite of mescaline in humans, but has little pharmacological activity of its own.^[2]^[4] At doses of 306 to 756 mg orally, only mild drowsiness was observed at the highest dose.^[2]^[4]^[5]^[3]^[6]^[7] Hence, N-acetylmescaline appears to be inactive as a hallucinogen.^[5] N-Acetylmescaline has microtubule assembly inhibitory activity.^[8] The chemical synthesis of N-acetylmescaline has been described.^[2] N-Acetylmescaline was isolated and first synthesized by Ernst Späth and Johann Bruck and was described by them in the scientific literature in 1938.^[3]^[9]

Other namesNAM; Mescaline acetamide; N-Acetyl-3,4,5-trimethoxyphenethylamine

CAS Number

4593-89-9

PubChem CID

100597

ChemSpider

90893

Quick facts Clinical data, Other names ...

N-Acetylmescaline
Clinical data

Other names	NAM; Mescaline acetamide; N-Acetyl-3,4,5-trimethoxyphenethylamine
Identifiers
IUPAC name N-[2-(3,4,5-trimethoxyphenyl)ethyl]acetamide
CAS Number	4593-89-9
PubChem CID	100597
ChemSpider	90893
UNII	U68P9VX8EK
CompTox Dashboard (EPA)	DTXSID10196660
Chemical and physical data
Formula	C₁₃H₁₉NO₄
Molar mass	253.298 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	93 to 94 °C (199 to 201 °F) ^[1]
SMILES O=C(NCCc1cc(OC)c(OC)c(OC)c1)C
InChI InChI=1S/C13H19NO4/c1-9(15)14-6-5-10-7-11(16-2)13(18-4)12(8-10)17-3/h7-8H,5-6H2,1-4H3,(H,14,15) Key:SNMFNOQKGANWHD-UHFFFAOYSA-N

References

[1]
Buckingham J, Macdonald F, eds. (1996). Dictionary of Natural Products. Vol. 6. Chapman & Hall. p. 3842. ISBN 978-0-412-54110-0.
[2]
Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "The N-acetyl analogue has been found in the peyote plant, and it is also a major metabolite of mescaline in man. It is made by the gentle reaction of mescaline with acetic anhydride (a bit too much heat, and the product N-acetyl mescaline will cyclize to a dihydroisoquinoline, itself a fine white crystalline solid, mp 160-161 °C) and can be recrystallized from boiling toluene. A number of human trials with this amide at levels in the 300 to 750 milligrams range have shown it to be with very little activity. At the highest levels there have been suggestions of drowsiness. Certainly there were none of the classic mescaline psychedelic effects."
[3]
Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6. 2.2.5. N-Acetylmescaline: N-Acetylmescaline (27) has been reported as a trace component of peyote (Späth and Bruck, 1938). It is also a trace metabolite of mescaline in man, appearing in the urine between the fifth and seventh hour following mescaline administration, and accounting for about 0.1% of the administered drug (Charalampous et al., 1966). This research group has explored the action of N-acetylmescaline (27) in normal humans and found it to be largely without effects in the dose range 300-750 mg, orally. At the highest dose explored, there was a report of a mild degree of drowsiness one hour following administration of the chemical.
[4]
Shulgin AT (1976). "Psychotomimetic Agents". In Gordon M (ed.). Psychopharmacological Agents. Vol. 4. Academic Press. p. 94. ISBN 978-0-323-15963-0.
[5]
Mangner TJ (1978). Potential Psychotomimetic Antagonists. N,n -diethyl-1-methyl-3-aryl-1, 2, 5, 6-tetrahydropyridine-5-carboxamides (Ph.D. thesis). University of Michigan. doi:10.7302/11268. Archived from the original on 30 March 2025. Two N-substituted mescaline analogs isolated from L. williamsii are N-methylmescaline (62a) and N-acetylmescaline (62b).95 N-Methylmescaline shows no central effects at a dose which would represent many times the level that would be encountered in a normal dose of peyote.67 N-Acetylmescaline, which has been identified as a metabolite of mescaline in man, is centrally inactive to 750 mg.96
[6]
Shulgin AT (1979). "Chemistry of phenethylamines related to mescaline". Journal of Psychedelic Drugs. 11 (1–2): 41–52. doi:10.1080/02791072.1979.10472091. PMID 522167. Archived from the original on 2025-07-12. Acetylmescaline was assayed at varying levels between 300 and 750 mg, and was without effect except for some drowsiness in some subjects at the highest levels.
[7]
Charalampous KD, Walker KE, Kinross-Wright J (1966). "Metabolic fate of mescaline in man". Psychopharmacologia. 9 (1): 48–63. doi:10.1007/BF00427703. PMID 5989103. Administration of N-acetylmescaline to human subjects In the course of our present studies we have administered N-acetylmescaline to several human subjects starting with a small dose and gradually increasing the amount. In addition we have included in this evalution a "double blind" design where four subjects received the following: one a dose of 306 mg of N-acetylmescaline (4.08 mg per kg); one, 450 mg (5.25 mg per kg); one, 675 mg (9.0 mg per kg); and one, 756 mg (10.4 mg per kg). None of these subjects experienced any behavioral or physiological effects with the exception of the last one, who one hour after the administration of N-acetylmescaline experienced a mild degree of drowsiness. [...] From our present studies it also appears that N-acetylmescaline is essentially inactive and that N-acetylation is another detoxication pathway for ingested mescaline.
[8]
Dumortier C, Potenziano JL, Bane S, Engelborghs Y (October 1997). "The mechanism of tubulin-colchicine recognition--a kinetic study of the binding of a bicyclic colchicine analogue with a minor modification of the A ring". European Journal of Biochemistry. 249 (1): 265–269. doi:10.1111/j.1432-1033.1997.t01-1-00265.x. PMID 9363778.
[9]
Späth E, Bruck J (6 June 1938). "N -Acetyl-mezcalin als Inhaltsstoff der Mezcal-buttons (XIX. Mitteil. über Kakteen-Alkaloide)". Berichte der Deutschen Chemischen Gesellschaft (A and B Series). 71 (6): 1275–1276. doi:10.1002/cber.19380710628. ISSN 0365-9488.

N-Acetylmescaline

See also

References

External links

Related Articles