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Ibogamine information


Ibogamine
Skeletal formula of ibogamine
Ball-and-stick model of the ibogamine molecule
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • [6R-(6α,6aβ,7β,9α)]-7-ethyl-6,6a,7,8,9,10,12,13-octahydro-6,9-methano-5H-pyrido[1',2':1,2]azepino[4,5-b]indole
CAS Number
  • 481-87-8 ☒N
PubChem CID
  • 100217
ChemSpider
  • 90568 checkY
ChEBI
  • CHEBI:5853 checkY
CompTox Dashboard (EPA)
  • DTXSID30963997 Edit this at Wikidata
Chemical and physical data
FormulaC19H24N2
Molar mass280.415 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • CC[C@H]1C[C@@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=CC=CC=C45
InChI
  • InChI=1S/C19H24N2/c1-2-13-9-12-10-16-18-15(7-8-21(11-12)19(13)16)14-5-3-4-6-17(14)20-18/h3-6,12-13,16,19-20H,2,7-11H2,1H3/t12-,13+,16+,19+/m1/s1 checkY
  • Key:LRLCVRYKAFDXKU-YGOSVGOTSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Ibogamine is an anti-convulsant, anti-addictive, CNS stimulant alkaloid found in Tabernanthe iboga and Crepe Jasmine (Tabernaemontana divaricata).[1][2][3] Basic research related to how addiction affects the brain has used this chemical.[4]

Ibogamine persistently reduced the self-administration of cocaine and morphine in rats.[5] The same study found that ibogamine (40 mg/kg) and coronaridine (40 mg/kg) did not produce "any tremor effects in rats that differ significantly from saline control". While the related alkaloids ibogaine (20–40 mg/kg), harmaline (10–40 mg/kg) and desethylcoronaridine (10–40 mg/kg) were "obviously tremorgenic".[5]

  1. ^ Bartlett MF, Dickel DF, Taylor WI (1958). "The Alkaloids of Tabernanthe iboga. Part IV.1 The Structures of Ibogamine, Ibogaine, Tabernanthine and Voacangine". Journal of the American Chemical Society. 80 (1): 126–136. doi:10.1021/ja01534a036.
  2. ^ Kuehne ME, Reider PJ (1985). "A synthesis of ibogamine". The Journal of Organic Chemistry. 50 (9): 1464–1467. doi:10.1021/jo00209a020.
  3. ^ Rastogi K, Kapil RS, Popli SP (January 1980). "New alkaloids from Tabernaemontana divaricata". Phytochemistry. 19 (6): 1209–1212. Bibcode:1980PChem..19.1209R. doi:10.1016/0031-9422(80)83085-8.
  4. ^ Levi MS, Borne RF (October 2002). "A review of chemical agents in the pharmacotherapy of addiction". Current Medicinal Chemistry. 9 (20): 1807–1818. doi:10.2174/0929867023368980. PMID 12369879.
  5. ^ a b Glick SD, Kuehne ME, Raucci J, Wilson TE, Larson D, Keller RW, Carlson JN (September 1994). "Effects of iboga alkaloids on morphine and cocaine self-administration in rats: relationship to tremorigenic effects and to effects on dopamine release in nucleus accumbens and striatum". Brain Research. 657 (1–2): 14–22. doi:10.1016/0006-8993(94)90948-2. PMID 7820611. S2CID 1940631.

and 27 Related for: Ibogamine information

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Ibogamine

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Ibogamine is an anti-convulsant, anti-addictive, CNS stimulant alkaloid found in Tabernanthe iboga and Crepe Jasmine (Tabernaemontana divaricata). Basic...

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Voacangine

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late-stage biosynthesis of (-)-voacangine in Tabernanthe iboga, a (-)-ibogamine-type alkaloid, has been elucidated via homology-guided transcriptome mining...

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Tabernaemontana divaricata

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produce many alkaloids including catharanthine, coronaridine, dregamine, ibogamine, tabersonine, voacangine, voacamine and voacristine. Ibogaine may occur...

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Ibogaine

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to become (-)-ibogaine. The first pathway begins with a P450 enzyme, ibogamine-10-hydroxylase (I10H), and methylation of noribogaine-10-Ο-methyltransferase...

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Tabernanthine

Last Update:

Compared to ibogaine, it binds weakly to σ1 and σ2 receptor. Coronaridine Ibogamine Voacangine Tabernaemontanine Tabernanthalog Bartlett MF, Dickel DF, Taylor...

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MDMA

Last Update:

5-MeO-DPT (The Light) DPT Ibogaine-related 18-MAC 18-MC Coronaridine Ibogaine Ibogamine ME-18-MC Noribogaine Tabernanthine Voacangine x-MET (Metocin) 4-HO-MET...

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Ketamine

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Esketamine Etoxadrol Eticyclidine Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Levomethadone Levomethorphan...

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Tabernanthe iboga

Last Update:

descending order) Ibogaine Iboxygaine Ibogaline Alloibogaine Catharanthine Ibogamine Noribogaine Voacangine Yohimbine Hydroxyibogamine 18-Methoxycoronaridine...

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LSD

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5-MeO-DPT (The Light) DPT Ibogaine-related 18-MAC 18-MC Coronaridine Ibogaine Ibogamine ME-18-MC Noribogaine Tabernanthine Voacangine x-MET (Metocin) 4-HO-MET...

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Ibogaline

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Tabernanthe iboga along with the related chemical compounds ibogaine, ibogamine, and other minor alkaloids. It is a relatively smaller component of Tabernanthe...

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Magnesium

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Esketamine Etoxadrol Eticyclidine Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Levomethadone Levomethorphan...

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Harmaline

Last Update:

liable to imprisonment for a term not exceeding eighteen months. Harmalol Ibogamine Tetrahydroharmine, a similar harmala alkaloid "Peganum Harmala pamphlet:...

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Pentobarbital

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Esketamine Etoxadrol Eticyclidine Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Levomethadone Levomethorphan...

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Phencyclidine

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5-MeO-DPT (The Light) DPT Ibogaine-related 18-MAC 18-MC Coronaridine Ibogaine Ibogamine ME-18-MC Noribogaine Tabernanthine Voacangine x-MET (Metocin) 4-HO-MET...

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Zinc

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Esketamine Etoxadrol Eticyclidine Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Levomethadone Levomethorphan...

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Aromatic compound

Last Update:

5-MeO-DPT (The Light) DPT Ibogaine-related 18-MAC 18-MC Coronaridine Ibogaine Ibogamine ME-18-MC Noribogaine Tabernanthine Voacangine x-MET (Metocin) 4-HO-MET...

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Tetrahydrocannabinol

Last Update:

5-MeO-DPT (The Light) DPT Ibogaine-related 18-MAC 18-MC Coronaridine Ibogaine Ibogamine ME-18-MC Noribogaine Tabernanthine Voacangine x-MET (Metocin) 4-HO-MET...

Word Count : 5365

Barbiturate

Last Update:

Esketamine Etoxadrol Eticyclidine Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Levomethadone Levomethorphan...

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Atropa belladonna

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5-MeO-DPT (The Light) DPT Ibogaine-related 18-MAC 18-MC Coronaridine Ibogaine Ibogamine ME-18-MC Noribogaine Tabernanthine Voacangine x-MET (Metocin) 4-HO-MET...

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Psychoactive drug

Last Update:

5-MeO-DPT (The Light) DPT Ibogaine-related 18-MAC 18-MC Coronaridine Ibogaine Ibogamine ME-18-MC Noribogaine Tabernanthine Voacangine x-MET (Metocin) 4-HO-MET...

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Haloperidol

Last Update:

Esketamine Etoxadrol Eticyclidine Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Levomethadone Levomethorphan...

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Glycine

Last Update:

Esketamine Etoxadrol Eticyclidine Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Levomethadone Levomethorphan...

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Diethyl ether

Last Update:

Esketamine Etoxadrol Eticyclidine Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Levomethadone Levomethorphan...

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Glutathione

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Esketamine Etoxadrol Eticyclidine Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Levomethadone Levomethorphan...

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Deliriant

Last Update:

5-MeO-DPT (The Light) DPT Ibogaine-related 18-MAC 18-MC Coronaridine Ibogaine Ibogamine ME-18-MC Noribogaine Tabernanthine Voacangine x-MET (Metocin) 4-HO-MET...

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Indole alkaloid

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divaricata contains indole alkaloids including catharanthine, conophylline, ibogamine, tabersonine and voacristine Psilocybe cubensis contains psilocybin and...

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Oneirogen

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dreaming[citation needed] Harmaline [citation needed] Hyoscyamine Ibogaine, Ibogamine, and Tabernanthe iboga Ilex guayusa can promote vivid dreams and aids...

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