Voacamine

Voacamine
Identifiers
	IUPAC name (6R,6aR,7R,11S)-methyl 7-ethyl-3-((2R,6S,8R,14S,E)-5-ethylidene-14-(methoxycarbonyl)-3-methyl-2,3,4,5,6,7,8,9-octahydro-1H-2,6-methanoazecino[5,4-b]indol-8-yl)-2-methoxy-6,6a,7,8,9,10,12,13-octahydro-5H-6,9-methanopyrido[1',2':1,2]azepino[4,5-b]indole-6-carboxylate;
CAS Number	3371-85-5 ;
PubChem CID	11953931;
DrugBank	DB04877 ;
ChemSpider	30808559 ;
UNII	2Z504YT5AG;
ChEMBL	ChEMBL445022 ;
CompTox Dashboard (EPA)	DTXSID20863159 ;
ECHA InfoCard	100.020.139
Chemical and physical data
Formula	C43H52N4O5
Molar mass	704.912 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC1CC2CC3(C1N(C2)CCC4=C3NC5=CC(=C(C=C45)OC)C6CC\7C(C(CC8=C6NC9=CC=CC=C89)N(C/C7=C/C)C)C(=O)OC)C(=O)OC;
	InChI InChI=1S/C43H52N4O5/c1-7-24-15-23-20-43(42(49)52-6)39-27(13-14-47(21-23)40(24)43)29-19-36(50-4)30(17-34(29)45-39)31-16-28-25(8-2)22-46(3)35(37(28)41(48)51-5)18-32-26-11-9-10-12-33(26)44-38(31)32/h8-12,17,19,23-24,28,31,35,37,40,44-45H,7,13-16,18,20-22H2,1-6H3/b25-8-/t23-,24+,28-,31+,35-,37-,40-,43-/m0/s1 ; Key:VCMIRXRRQJNZJT-XBBWQDJOSA-N ;
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Voacamine, also known under the older names voacanginine and vocamine, is a naturally occurring dimeric indole alkaloid of the secologanin type, found in a number of plants, including Voacanga africana and Tabernaemontana divaricata. It is approved for use as an antimalarial drug in several African countries.^[1] Voacamine exhibits cannabinoid CB1 receptor antagonistic activity.^[2]

Chemistry

Structure

There is considerable confusion about the absolute stereochemical configuration of voacamine and the originally published absolute structure had to be later revised.^[3]^[4] It has an ibogaine unit joined with vobasine unit.

Adverse Effect

Voacamine can cause hypertension in high dose.^[5]

References

^ "Voacamine". DrugBank. Canadian Institutes of Health Research.
^ Kitajima M, Iwai M, Kikura-Hanajiri R, Goda Y, Iida M, Yabushita H, Takayama H (April 2011). "Discovery of indole alkaloids with cannabinoid CB1 receptor antagonistic activity". Bioorganic & Medicinal Chemistry Letters. 21 (7): 1962–4. doi:10.1016/j.bmcl.2011.02.036. PMID 21376588.
^ Kutney JP, Brown RT, Piers E (March 1966). "The absolute configuration of the Iboga alkaloids". Canadian Journal of Chemistry. 44 (5): 637–9. doi:10.1139/v66-087.
^ Kutney JP, Fuji K, Treasurywala AM, Fayos J, Clardy J, Scott AI, Wei CC (1973). "Structure and Absolute Configuration of (+)-Coronaridine Hydrobromide. A Comment on the Absolute Configuration of the Iboga Alkaloids". J. Am. Chem. Soc. 95 (16): 5407–5409. doi:10.1021/ja00797a049.
^ Leeuwenberg AJ (1985). "oacanga, (Apocynaceae), a review of its taxonomy, phytochemistry, ethnobotany and pharmacology". Agric. Univ. Wagenigen. pp. 85–3.

[1] "Voacamine". DrugBank. Canadian Institutes of Health Research.

[2] Kitajima M, Iwai M, Kikura-Hanajiri R, Goda Y, Iida M, Yabushita H, Takayama H (April 2011). "Discovery of indole alkaloids with cannabinoid CB1 receptor antagonistic activity". Bioorganic & Medicinal Chemistry Letters. 21 (7): 1962–4. doi:10.1016/j.bmcl.2011.02.036. PMID 21376588.

[3] Kutney JP, Brown RT, Piers E (March 1966). "The absolute configuration of the Iboga alkaloids". Canadian Journal of Chemistry. 44 (5): 637–9. doi:10.1139/v66-087.

[4] Kutney JP, Fuji K, Treasurywala AM, Fayos J, Clardy J, Scott AI, Wei CC (1973). "Structure and Absolute Configuration of (+)-Coronaridine Hydrobromide. A Comment on the Absolute Configuration of the Iboga Alkaloids". J. Am. Chem. Soc. 95 (16): 5407–5409. doi:10.1021/ja00797a049.

[5] Leeuwenberg AJ (1985). "oacanga, (Apocynaceae), a review of its taxonomy, phytochemistry, ethnobotany and pharmacology". Agric. Univ. Wagenigen. pp. 85–3.

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Identifiers

IUPAC name (6R,6aR,7R,11S)-methyl 7-ethyl-3-((2R,6S,8R,14S,E)-5-ethylidene-14-(methoxycarbonyl)-3-methyl-2,3,4,5,6,7,8,9-octahydro-1H-2,6-methanoazecino[5,4-b]indol-8-yl)-2-methoxy-6,6a,7,8,9,10,12,13-octahydro-5H-6,9-methanopyrido[1',2':1,2]azepino[4,5-b]indole-6-carboxylate
CAS Number	3371-85-5^N
PubChem CID	11953931
DrugBank	DB04877^N
ChemSpider	30808559^N
UNII	2Z504YT5AG
ChEMBL	ChEMBL445022^N
CompTox Dashboard (EPA)	DTXSID20863159
ECHA InfoCard	100.020.139
Chemical and physical data
Formula	C₄₃H₅₂N₄O₅
Molar mass	704.912 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCC1CC2CC3(C1N(C2)CCC4=C3NC5=CC(=C(C=C45)OC)C6CC\7C(C(CC8=C6NC9=CC=CC=C89)N(C/C7=C/C)C)C(=O)OC)C(=O)OC
InChI InChI=1S/C43H52N4O5/c1-7-24-15-23-20-43(42(49)52-6)39-27(13-14-47(21-23)40(24)43)29-19-36(50-4)30(17-34(29)45-39)31-16-28-25(8-2)22-46(3)35(37(28)41(48)51-5)18-32-26-11-9-10-12-33(26)44-38(31)32/h8-12,17,19,23-24,28,31,35,37,40,44-45H,7,13-16,18,20-22H2,1-6H3/b25-8-/t23-,24+,28-,31+,35-,37-,40-,43-/m0/s1^N Key:VCMIRXRRQJNZJT-XBBWQDJOSA-N^N
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Voacamine

Chemistry

Structure

Adverse Effect

See also

References

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