Trichocereine

Trichocereine

File:Trichocereine.svg
Clinical data
Other names	N,N-Dimethyl-3,4,5-trimethoxyphenethylamine; N,N-Dimethylmescaline; 3,4,5-Trimethoxy-N,N-dimethylbenzeneethanamine; MM-M
ATC code	None
Identifiers
IUPAC name N,N-dimethyl-2-(3,4,5-trimethoxyphenyl)ethanamine
CAS Number	529-91-9 checkY
PubChem CID	420418
ChemSpider	372161
ChEMBL	ChEMBL2009417
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C13H21NO3
Molar mass	239.315 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN(C)CCC1=CC(=C(C(=C1)OC)OC)OC
InChI InChI=1S/C13H21NO3/c1-14(2)7-6-10-8-11(15-3)13(17-5)12(9-10)16-4/h8-9H,6-7H2,1-5H3 Key:BTSKBPJWJZFTPQ-UHFFFAOYSA-N

Trichocereine, or trichocerine, also known as N,N-dimethyl-3,4,5-trimethoxyphenethylamine or as N,N-dimethylmescaline (MM-M), is a phenethylamine alkaloid that is found in several cacti and other plant species and is closely related to the psychedelic drug mescaline (3,4,5-trimethoxyphenethylamine).

Use and effects

In contrast to mescaline, trichocereine has been found to lack psychoactive effects in humans even at large doses. F. P. Ludueña assessed trichocereine hydrochloride in the mid-1930s and found that it produced no effects, with the exception of slight gastric heaviness, at doses of up 9 mg/kg orally (630 mg for a 70-kg person) and up to 550 mg parenterally. Vojtĕchovský and Krus assessed trichocereine in the 1960s at doses of up to 800 mg (presumably orally) and found that they were weaker than those of 400 mg mescaline. They also tried 400 mg sublingually and reported that it produced moderate psychedelic effects with a one-hour onset (compared to two hours for mescaline) and a "proportionally shorter" duration than mescaline or a duration of one hour. Per Alexander Shulgin however, these psychoactive effects were ill-defined and it was felt that they might have been attributable to anxiety.

Shulgin has noted that Trichocereus terscheckii, which contains trichocereine as its major constituent, is commonly consumed in large amounts by humans and animals as a water source without obvious consequences. It has been noted that N-methylation of psychedelic phenethylamines, for instance Beatrice (N-methyl-DOM), has invariably eliminated their hallucinogenic activity.

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

Trichocereine showed no activity in the conditioned avoidance test in rodents. It has been reported to substitute for mescaline in rodent drug discrimination tests. Trichocereine at a dose of 50 mg/kg intraperitoneally produced full substitution for mescaline (25 mg/kg) in these tests, whereas it only transiently substituted for mescaline when given intracerebroventricularly. It produces convulsions in cats and causes marked excitation similar to that induced by amphetamine in rodents.

Chemistry

Synthesis

The chemical synthesis of trichocereine has been described.

Natural occurrence

Trichocereine was first reported in the Trichocereus terscheckii cactus in 1935 and was subsequently isolated from Gymnocalycium spp. and Turbinicarpus spp. cacti. Additionally, it has been found in the shrubs Acacia berlandieri and Acacia rigidula. The compound is the major alkaloid present in Trichocereus terscheckii. It has never been reported in peyote (Lophophora williamsii).

History

Trichocereine was first described in the scientific literature by F. P. Ludueña by 1935.

Society and culture

Legal status

United States

Trichocereine is not an explicitly controlled substance in the United States as of 2011.

See also

• Substituted mescaline analogue
• N-Methylmescaline
• Methyl-TMA (N-methyl-TMA)
• Macromerine
• 3-Hydroxy-N,N-dimethylphenethylamine (LSM-6)
• N-Methyl-DOET
• N-Formylmescaline
• N,N-Diformylmescaline
• N-Acetylmescaline

External links

• Trichocereine - Isomer Design
• Trichocereine - The Shulgin Index
• N,N-Dimethylmescaline (Trichocereine) - Trout's Notes