Voacamine, also known under the older names voacanginine and vocamine, is a naturally occurring dimeric

indole alkaloid Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known differe ...

of the

secologanin Secologanin is a secoiridoid monoterpene synthesized from geranyl pyrophosphate in the mevalonate pathway. Secologanin then proceeds with dopamine or tryptamine to form ipecac and terpene indole alkaloids, respectively. Biosynthesis Secologanin b ...

type, found in a number of plants, including ''

Voacanga africana ''Voacanga africana'' is a small tree native to tropical Africa belonging to the family Apocynaceae that grows to in height and bears leaves that are up to in length. The yellow or white flowers are succeeded by paired, follicular, dehiscent f ...

'' and ''

Tabernaemontana divaricata ''Tabernaemontana divaricata'', commonly called pinwheel flower, crape jasmine, East India rosebay, and Nero's crown, is an evergreen shrub or small tree native to South Asia, Southeast Asia and China. In zones where it is not hardy it is grown a ...

''. It is approved for use as an

antimalarial drug Antimalarial medications or simply antimalarials are a type of antiparasitic chemical agent, often naturally derived, that can be used to treat or to prevent malaria, in the latter case, most often aiming at two susceptible target groups, young c ...

in several African countries. Voacamine exhibits

cannabinoid Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...

CB1 receptor Cannabinoid receptor type 1 (CB1), also known as cannabinoid receptor 1, is a G protein-coupled cannabinoid receptor that in humans is encoded by the ''CNR1'' gene. The human CB1 receptor is expressed in the peripheral nervous system and central ...

antagonistic activity.

Chemistry

Structure

There is considerable confusion about the absolute stereochemical configuration of voacamine and the originally published absolute structure had to be later revised. It has an

ibogaine Ibogaine is a naturally occurring psychoactive substance found in plants in the family Apocynaceae such as ''Tabernanthe iboga'', ''Voacanga africana'', and ''Tabernaemontana undulata''. It is a psychedelic with dissociative properties. Prel ...

unit joined with

vobasine Vobasine is a naturally occurring monoterpene indole alkaloid found in several species in the genus ''Tabernaemontana'' including ''Tabernaemontana divaricata''. History Vobasine was first reported by Renner in 1959 after its isolation from ''Voac ...

unit.

Adverse Effect

Voacamine can cause

hypertension Hypertension (HTN or HT), also known as high blood pressure (HBP), is a long-term medical condition in which the blood pressure in the arteries is persistently elevated. High blood pressure usually does not cause symptoms. Long-term high bl ...

in high dose.

References

{{Reflist Indole alkaloids Antimalarial agents

Chemistry

Structure

Adverse Effect

See also

References