Chanoclavine

Chanoclavine
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
CAS Number	2390-99-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	4444739;
PubChem CID	5281381;
UNII	32X6F73RE2 ;
CompTox Dashboard (EPA)	DTXSID50893242 ;
	InChI 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;
	SMILES C/C(=C\[C@H]1[C@@H](CC2=CNC3=CC=CC1=C23)NC)/CO;
Properties
Chemical formula	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). Infobox references

Chanoclavine, also known as chanoclavin-l is a tri-cyclic 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]

References

^ 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. doi:10.1016/j.phytochem.2009.05.023. PMID 19695648.
^ 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.

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[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. 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.

[1]

[2]

Chanoclavine

See also

References