Chanoclavine

Last updated
Chanoclavine
Chanoclavine.svg
Names
IUPAC name
[9(9a)E]-9-Methyl-9,9a-didehydro-7,8-seco-9a-homoergolin-8-ol
Systematic IUPAC name
(2E)-2-Methyl-3-[(4R,5R)-4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl]prop-2-en-1-ol
Other names
chanoclavin-l
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C16H20N2O/c1-10(9-19)6-13-12-4-3-5-14-16(12)11(8-18-14)7-15(13)17-2/h3-6,8,13,15,17-19H,7,9H2,1-2H3/b10-6+/t13-,15-/m1/s1
    Key: SAHHMCVYMGARBT-HEESEWQSSA-N
  • InChI=1/C16H20N2O/c1-10(9-19)6-13-12-4-3-5-14-16(12)11(8-18-14)7-15(13)17-2/h3-6,8,13,15,17-19H,7,9H2,1-2H3/b10-6+/t13-,15-/m1/s1
    Key: SAHHMCVYMGARBT-HEESEWQSBR
  • C/C(=C\[C@H]1[C@@H](CC2=CNC3=CC=CC1=C23)NC)/CO
Properties
C16H20N2O
Molar mass 256.34 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Chanoclavine, also known as chanoclavin-I, is a tricyclic ergot alkaloid (ergoline) isolate of certain fungi. It is mainly produced by members of the genus Claviceps . [1] Long used in traditional Chinese medicine, it was found in 1987 mouse studies to stimulate dopamine D2 receptors in the brain. [2] It is described as being devoid of ergot-like activity, possessing no outstanding pharmacological activity, and as not contributing to the hallucinogenic effects of morning glory seeds. [3] [4] [5] [6] [7] [8]

See also

References

  1. Lorenz, N; Haarmann, T; Pazoutová, S; Jung, M; Tudzynski, P (2009). "The ergot alkaloid gene cluster: Functional analyses and evolutionary aspects". Phytochemistry. 70 (15–16): 1822–32. Bibcode:2009PChem..70.1822L. doi:10.1016/j.phytochem.2009.05.023. PMID   19695648.
  2. Watanabe, H; Somei, M; Sekihara, S; Nakagawa, K; Yamada, F (1987). "Dopamine receptor stimulating effects of chanoclavine analogues, tricyclic ergot alkaloids, in the brain". Japanese Journal of Pharmacology. 45 (4): 501–6. doi: 10.1254/jjp.45.501 . PMID   3127619.
  3. Hofmann A (1963). "The Active Principles of the Seeds of Rivea Corymbosa and Ipomoea Violacea". Botanical Museum Leaflets, Harvard University. 20 (6). Harvard University Herbaria: 194–212. doi:10.5962/p.168542. ISSN   0006-8098. JSTOR   41762231. Archived from the original on 28 March 2025. [...] chanoclavine, which has no outstanding pharmacological activity, appears to play no part in the occurrence of the psychic effects of badoh and badoh negro.
  4. Albert Hofmann (1968). "Psychotomimetic Agents". In Burger A (ed.). Drugs Affecting the Central Nervous System. Vol. 2. New York: M. Dekker. pp. 169–235. OCLC   245452885. OL   13539506M. Furthermore, chanoclavine, which has no outstanding pharmacological activity, appears to play no part in the occurrence of the psychic effects of ololiuqui.
  5. Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN   978-0-85608-011-1. OCLC   2176880. OL   4850660M. d-Lysergic acid amide (ergine) is the major constituent of the seeds of both Rivea corymbosa and Ipomoea violacea, together with smaller amounts of d-isolysergic acid amide (isoergine), chanoclavine, elymoclavine, and the N-(1-hydroxyethyl)amides of lysergic and isolysergic acids. [...] It is clear that the pharmacologically active constituents of ololiuqui are the isomeric lysergic acid amides. [...] Heim and his colleagues suggest that the overall effects of ololiuqui are due to these two compounds, the d-lysergic acid amide giving intoxication with strong autonomic side-effects and the d-isolysergic acid amide producing some euphoria, synaesthesia, and altered time experience. Certainly elymoclavine, lysergol, chanoclavine, and ergometrine produce no psychic changes in man (Isbell and Gorodetzky, 1966; Hofmann, 1968), though the first two do produce central excitation in animals (Yui and Takeo, 1958).
  6. Heacock RA (1975). "Psychotomimetics of the Convolvulaceae". Prog Med Chem. Progress in Medicinal Chemistry. 11: 91–118. doi:10.1016/s0079-6468(08)70209-1. ISBN   978-0-7204-7411-4. PMID   1078534. Archived from the original on 30 March 2025. No psychological effects have been reported for ergometrine (6), a drug widely used in obstetrics, nor for chanoclavine (3).
  7. Fanchamps A (1978). "Some Compounds With Hallucinogenic Activity". In Berde B, Schild HO (eds.). Ergot Alkaloids and Related Compounds. Handbook of Experimental Pharmacology (HEP). Vol. 49. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 567–614. doi:10.1007/978-3-642-66775-6_8. ISBN   978-3-642-66777-0. Archived from the original on 30 March 2025. The last component, Chanoclavine, is a tricyclic alkaloid, which is devoid of ergot-like activities. [...] Table 2. Psychotomimetic activity and some pharmacodynamic effects of structural analogues of LSD [...]
  8. Hofmann A (January–March 1971). "Teonanácatl and Ololiuqui, two ancient magic drugs of Mexico". Bulletin on Narcotics. 23 (1): 3–14. Archived from the original on 28 March 2025. Furthermore, chanoclavine, which has no outstanding pharmacological activity, appears to play no part in the occurrence of the psychic effects of ololiuqui.