Voacangine (12-methoxyibogamine-18-carboxylic acid methyl ester) is an

alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...

found predominantly in the root bark of the ''

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 ...

'' tree, as well as in other plants such as ''

Tabernanthe iboga ''Tabernanthe iboga'' (iboga) is an evergreen rainforest shrub native to Central Africa. A member of the Apocynaceae family indigenous to Gabon, the Democratic Republic of Congo, and the Republic of Congo, it is cultivated across Central Africa ...

'', ''

Tabernaemontana africana ''Tabernaemontana africana'' is a species of plant in the Apocynaceae family. It is found in tropical Africa. It is an evergreen perennial shrub with a maximum height of 6 meters. The plant can be used to produce latex Latex is an emulsio ...

'', ''

Trachelospermum jasminoides ''Trachelospermum jasminoides'' is a species of flowering plant in the family (biology), family Apocynaceae, native plant, native to eastern and southeastern Asia (Japan, Korea, southern China and Vietnam).Flora of China''Trachelospermum jasmino ...

'', ''

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 ...

'' and ''

Ervatamia yunnanensis ''Tabernaemontana'' is a genus of flowering plants in the family Apocynaceae. It has a pan-tropical distribution, found in Asia, Africa, Australia, North America, South America, and a wide assortment of oceanic islands. These plants are evergreen ...

''. It is an iboga

which commonly serves as a precursor for the semi-synthesis of

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 ...

. It has been demonstrated in animals to have similar anti-addictive properties to ibogaine itself. It also potentiates the effects of

barbiturates Barbiturates are a class of depressant drugs that are chemically derived from barbituric acid. They are effective when used medically as anxiolytics, hypnotics, and anticonvulsants, but have physical and psychological addiction potential as ...

. Under UV-A and UV-B light its crystals fluoresce blue-green, and it is soluble in

ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...

Pharmacology

Pharmacodynamics

Voacangine exhibits

AChE Ache or Aches may refer to: Ethnography * Aché, an indigenous people of eastern Paraguay * Aché language, the language of the Aché people * Ache language (China) * Aṣẹ (Cuban spelling: ''aché''), a concept in Orisha belief People * Ach ...

inhibitory activity. Docking simulation reveals that it has inhibitory effect on VEGF2 kinase and reduces

angiogenesis Angiogenesis is the physiological process through which new blood vessels form from pre-existing vessels, formed in the earlier stage of vasculogenesis. Angiogenesis continues the growth of the vasculature by processes of sprouting and splitting ...

. Like ibogaine, its a potent HERG blocker in vitro. It also acts as antagonist to

TRPM8 Transient receptor potential cation channel subfamily M (melastatin) member 8 (TRPM8), also known as the cold and menthol receptor 1 (CMR1), is a protein that in humans is encoded by the ''TRPM8'' gene. The TRPM8 channel is the primary molecular ...

and

TRPV1 The transient receptor potential cation channel subfamily V member 1 (TrpV1), also known as the capsaicin receptor and the vanilloid receptor 1, is a protein that, in humans, is encoded by the ''TRPV1'' gene. It was the first isolated member of th ...

receptor but agonist of

TRPA1 Transient receptor potential cation channel, subfamily A, member 1, also known as transient receptor potential ankyrin 1, TRPA1, or The Wasabi Receptor, is a protein that in humans is encoded by the ''TRPA1'' (and in mice and rats by the ''Trpa1' ...

Pharmacokinetics

The absolute bioavailability of voacangine is around 11-13%.

Side effects

High doses of voacangine produce convulsions and asphyxia.

References

{{Reflist, 2 Indole alkaloids Alkaloids found in Iboga HERG blocker Drug rehabilitation Methyl esters Phenol ethers Carboxylate esters

Pharmacology

Pharmacodynamics

Pharmacokinetics

Side effects

See also

References