Trichocereine, ortrichocerine, also known asN,N-dimethyl-3,4,5-trimethoxyphenethylamine or asN,N-dimethylmescaline (MM-M), is aphenethylaminealkaloid that is found in severalcacti and other plant species and is closely related to thepsychedelic drugmescaline (3,4,5-trimethoxyphenethylamine).[1][2]
In contrast to mescaline, trichocereine has been found to lackpsychoactive effects in humans even at large doses.[3][4][5][6] Ludueña assessed trichocereinehydrochloride in the mid-1930s and found that it produced no effects, with the exception of slight gastric heaviness, at doses of up 9mg/kgorally (630mg for a 70-kg person) and up to 550mgparenterally.[5][1][3][4][7][2][8] Vojtĕchovský and Krus assessed trichocereine in the 1960s at doses of up to 800mg (presumably orally) and found that they were weaker than those of 400mg mescaline.[3][9] They also tried 400mgsublingually and reported that it produced moderate psychedelic effects with a one-houronset (compared to two hours for mescaline) and a "proportionally shorter"duration than mescaline or a duration of one hour.[3][4][9] PerAlexander Shulgin however, these psychoactive effects were ill-defined and it was felt that they might have been attributable toanxiety.[3][4]
Shulgin has noted thatTrichocereus 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.[3][4] It has been noted thatN-methylation of psychedelic phenethylamines, for instanceBeatrice (N-methyl-DOM), has invariably eliminated their hallucinogenic activity.[10][6]
^abcdLuduena, F.P. (1935) Pharmacology of trichocereine, an alkaloid from the cactus Trichocereus terscheki (Parm.) Britton and Rose.Revista de la Sociedad Argentina de Biologia 11: 604–610.
^abcdefghShulgin 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.ISBN978-1-4757-0512-6.2.2.2. N,N-Dimethylmescaline: N,N-Dimethylmescaline (24, trichocerine) has never been observed in peyote, although the 3-O-demethylated homolog is present and has been studied in biosynthetic schemes (Lundstrom, 1971b). The compound has been reported as the major component of the mescaline-containing cactus Trichocerius terscheckii (Reti, 1939; Reti and Castrillon, 1951). The fact that both animals and man can, with impunity, drink the fluids from the crushed pulp of this plant has prompted a study into the psychopharmacological properties of trichocerine. Luduena (1935, 1936) in a single acute experiment consumed 550 mg of the trichocerine hydrochloride and noted no effects of a sensory nature, only a slight gastric heaviness. Vojtechovsky and Krus (1967) have reported that this base has less than one-half the potency of mescaline in humans. At doses of up to 800 mg, with one exception, all responses were weaker than those noted for a 400 mg challenge of mescaline. A 400 mg trial with trichocerine via the perlingual route showed a moderate psychodysleptic effect with a one-hour latency (mescaline required two hours with this mode of absorption). The duration of symptoms was proportionally shorter.
^abcdefgShulgin AT (1979)."Chemistry of phenethylamines related to mescaline".J Psychedelic Drugs.11 (1–2):41–52.doi:10.1080/02791072.1979.10472091.PMID522167.The N,N-dimethyl homolog, trichocerine, is the major component of another cactus Trichocereus terscheckii. This compound is without activity in humans even in large quantities, as shown by direct experimentation and by the fact that the plant from which it comes is commonly used as a water source by both humans and animals. This alkaloid has never been reported to be in Peyote. [...] Trichocerine, although not in Peyote, is a major component of other cacti and is a valid nitrogen-substituted homolog of mescaline. In studies with acute dosages of up to 800 mg there is some gastric heaviness noted but no changes of the visual or interpretive state. One study of 400 mg administered sublingually led to the observation of some ill-defined psychotropic disturbances for about an hour, but it was felt that these might be ascribable to anxiety.
^abShulgin AT (March 1973)."Mescaline: the chemistry and pharmacology of its analogs".Lloydia.36 (1):46–58.PMID4576313.The homologous N,N-dimethylmescaline (trichocerine, 8) has never been observed in peyote, although it has been observed in a number of closely related cacti. It has been included in this report because of its close relationship to the well-documented presence of the mono-methyl homolog, and the known presence of methylating enzymes in the peyote plant. The compound has been found devoid of any central activity in humans even following parenterally administered dosages of more than 500 mg (19). [...] 19. LUDUENA, F. P. 1936. Pharmacology of trichocerine, an alkaloid from the cactus. C. R. Soc. Biol. 121: 368.
^abcPatel AR (1968). "Mescaline and Related Compounds".Fortschritte der Arzneimittelforschung. Vol. 11. pp. 11–47.doi:10.1007/978-3-0348-7062-7_1.ISBN978-3-0348-7064-1.PMID4873202.LUDUENA [360] found that trichocereine (N,N-dimethylmescaline) acts on the C.N.S. and produces convulsions in normal cats but not in decerebrated cats. It does not produce mental disturbances in man. SMYTHIES and SYKES [361, 362] found that unlike mescaline, trichocereine causes negligible inhibition of the conditioned avoidance response and marked excitation similar to that produced by amphetamine. Increasing the dosage delays the onset of the excitation.
^abLuduena, F.-P. (1936) Comptes Rendus Hebdomaires des Séances et Mémoires de la Sociéte de Biologie et de ses Filiales et Associées (Sociéte de Biologie de Rosario 1935) 121: 368–369. “Pharmacologie de la Trichocéréine. Alcaloïde du Trichocereus terschecki (Parm.) Britton et Rose.”
^abVojtĕchovský M, Krus D (November 1967). "Psychotropic effect of mescaline-like drugs".Act Nerv Super (Praha).9 (4):381–383.PMID4889069.
^Smythies JR, Sykes EA (1966). "Structure-activity relationship studies on mescaline: the effect of dimethoxyphenylethylamine and N:N-dimethyl mescaline on the conditioned avoidance response in the rat".Psychopharmacologia.8 (5):324–330.doi:10.1007/BF00453510.PMID5923938.
