Anhalinine
Chemical compound
From Wikipedia, the free encyclopedia
Anhalinine, also known as O-methylanhalamine or mescaline-CR, is a tetrahydroisoquinoline alkaloid found in Lophophora williamsii (peyote) and other cacti.[2][3] It is structurally related to mescaline and is a cyclized phenethylamine analogue of mescaline.[2] Anhalinine is also pharmacologically active, but is only a minor constituent of peyote and is unlikely to contribute to its effects.[4][2][5][6]
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| Names | |
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| Preferred IUPAC name
6,7,8-Trimethoxy-1,2,3,4-tetrahydroisoquinoline | |
| Other names
O-Methylanhalamine; 6,7,8-Trimethoxy-THIQ; Anhalanine; Mescaline-CR | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C12H17NO3 | |
| Molar mass | 223.272 g·mol−1 |
| Melting point | 60–61 °C (140–142 °F; 333–334 K)[1] |
| Boiling point | 144–145 °C (291–293 °F; 417–418 K)[1] at 0.1 Torr |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Simple isoquinoline alkaloids of mescaline-containing cacti like anhalinine have received relatively little investigation.[2] Arthur Heffter found many of them to produce no effects similar to those of mescaline.[2] However, some of them have been found to produce convulsions in animals at high doses.[2] Anhalinine specifically has been described as having "stimulant" properties due to inhibiting cholinergic neurotransmission.[7][5][8][2] Alexander Shulgin tried anhalinine at small doses of 0.5 to 4.3 mg but experienced no effects.[9]
Anhalinine has been found to act as a low-potency inverse agonist of the serotonin 5-HT7 receptor, with an EC50 of 2,722 nM and an Emax of –85%.[10] This was much less potent in terms of this action than certain other tetrahydroisoquinolines like pellotine and anhalidine.[10] Serotonin 5-HT7 receptor inverse agonism might be involved in the sedative and hypnotic effects of certain peyote alkaloids like pellotine and anhalonidine.[11]
Anhalinine was first isolated from peyote by Ernst Späth in 1935.[12][6][13] Shulgin bioassayed it in 1963.[9]
Analogues
Cyclized tetrahydroisoquinoline analogues of other psychoactive phenethylamines, besides anhalinine (mescaline-CR), are also known, for instance AMPH-CR, METH-CR, PMMA-CR, DOM-CR, DOB-CR, MDA-CR, and MDMA-CR, among others.[14][15][16][17] In general, cyclization into tetrahydroisoquinolines results in abolition of their defining psychoactive effects and activities.[14][15][16][17] However, some tetrahydroisoquinolines show interactions with α2-adrenergic receptors and serotonin 5-HT1D, 5-HT6, and/or 5-HT7 receptors as well as effects related to these actions.[14][15][11][10]