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Trichocereine

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Trichocereine
Names
IUPAC name
N,N-dimethyl-2-(3,4,5-trimethoxyphenyl)ethanamine
Other names
N,N-Dimethyl-3,4,5-trimethoxyphenethylamine; N,N-Dimethylmescaline; 3,4,5-Trimethoxy-N,N-dimethylbenzeneethanamine; MM-M
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • 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
  • CN(C)CCC1=CC(=C(C(=C1)OC)OC)OC
Properties
C13H21NO3
Molar mass 239.31 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 plant species and is closely related to mescaline (3,4,5-trimethoxyphenethylamine).[1][2] It was first reported in the Trichocereus terscheckii cactus in 1935 and was subsequently isolated from Gymnocalycium spp. and Turbinicarpus spp. cacti.[1][2] Additionally, it has been found in the shrubs Acacia berlandieri and Acacia rigidula.[1] The compound is the major alkaloid present in Trichocereus terscheckii.[3][4] It has never been reported in peyote (Lophophora williamsii).[3][4]

The compound showed no activity in the conditioned avoidance test in rodents.[1][5][6] It has been reported to substitute for mescaline in rodent drug discrimination tests.[6] Trichocereine at a dose of 50 mg/kg intraperitoneally produced full substitution for mescaline (25 kg/kg) in these tests, whereas it only transiently substituted for mescaline when given intracerebroventricularly.[6] It produces convulsions in cats and causes marked excitation similar to that induced by amphetamine in rodents.[5][7][8][9]

In contrast to mescaline, trichocereine has been found to lack psychoactive effects in humans even at large doses.[3][4][10][11] 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.[10][1][3][4][5][2][7] 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.[12][3] 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.[3][4] Per Alexander Shulgin however, these psychoactive effects were ill-defined and it was felt that they might have been attributable to anxiety.[3][4]

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.[3][4] Keeper Trout has noted that N-methylation of psychedelic phenethylamines, for instance Beatrice (N-methyl-DOM), has invariably eliminated their hallucinogenic activity.[11]

See also

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References

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  1. ^ a b c d e Shulgin A, Manning T, Daley PF (2011). "#125. Trichocereine". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 309–310. ISBN 978-0-9630096-3-0. OCLC 709667010.
  2. ^ a b c Luduena, 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.
  3. ^ a b c d e f g h 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. 2.2.2. 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.
  4. ^ a b c d e f g Shulgin AT (1979). "Chemistry of phenethylamines related to mescaline". J Psychedelic Drugs. 11 (1–2): 41–52. doi:10.1080/02791072.1979.10472091. PMID 522167. 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.
  5. ^ a b c Patel AR (1968). "Mescaline and related compounds". Fortschr Arzneimittelforsch. 11: 11–47. doi:10.1007/978-3-0348-7062-7_1. PMID 4873202. 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.
  6. ^ a b c Browne RG, Harris RT, Ho BT (1974). "Stimulus properties of mescaline and N-methylated derivatives: difference in peripheral and direct central administration". Psychopharmacologia. 39 (1): 43–56. doi:10.1007/BF00421457. PMID 4425137.
  7. ^ a b Luduena, 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.”
  8. ^ Smythies, J. R., & Sykes, E. A. (1965, January). Structure-activity relationship studies of mescaline analogs on conditioned avoidance response in rats. Federation Proceedings, 24(2), 196. https://scholar.google.com/scholar?cluster=13792224556276262429
  9. ^ 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. PMID 5923938.
  10. ^ a b Shulgin AT (March 1973). "Mescaline: the chemistry and pharmacology of its analogs". Lloydia. 36 (1): 46–58. PMID 4576313. 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.
  11. ^ a b Keeper Trout & friends (2013). Trout’s Notes on The Cactus Alkaloids Nomenclature, Physical properties, Pharmacology & Occurrences (Sacred Cacti Fourth Edition, Part C: Cactus Chemistry: Section 1) (PDF). Mydriatic Productions/Better Days Publishing.
  12. ^ Vojtĕchovský M, Krus D (November 1967). "Psychotropic effect of mescaline-like drugs". Act Nerv Super (Praha). 9 (4): 381–383. PMID 4889069.
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