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Ibogamine

From Wikipedia, the free encyclopedia
Anti-convulsant, anti-addictive CNS stimulant alkaloid
Pharmaceutical compound
Ibogamine
Skeletal formula of ibogamine
Ball-and-stick model of the ibogamine molecule
Clinical data
ATC code
  • none
Identifiers
  • [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
PubChemCID
ChemSpider
ChEBI
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC19H24N2
Molar mass280.415 g·mol−1
3D model (JSmol)
  • CC[C@H]1C[C@@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=CC=CC=C45
  • 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 ananti-convulsant,anti-addictive, CNS stimulantalkaloid found inTabernanthe iboga and Crepe Jasmine (Tabernaemontana divaricata).[1][2][3]Basic research related to howaddiction 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) andcoronaridine (40 mg/kg) did not produce "anytremor effects in rats that differ significantly from saline control". While the related alkaloidsibogaine (20–40 mg/kg),harmaline (10–40 mg/kg) anddesethylcoronaridine (10–40 mg/kg) were "obviously tremorgenic".[5]

Pharmacology

[edit]

Like ibogaine, it has seems to have similar pharmacology. It has effects onKOR,[6]NMDAR,nAChR[7] and serotonin sites.[8] It also inhibits acetylcholinesterase and butyrylcholinesterase.[9]

Chemistry

[edit]

Synthesis

[edit]

Ibogamine can be prepared from one-step demethoxycarbonylation process throughcoronaridine.[10]

See also

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References

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  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. ^abGlick 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.
  6. ^Deecher DC, Teitler M, Soderlund DM, Bornmann WG, Kuehne ME, Glick SD (February 1992). "Mechanisms of action of ibogaine and harmaline congeners based on radioligand binding studies".Brain Research.571 (2):242–247.doi:10.1016/0006-8993(92)90661-R.PMID 1377086.S2CID 17159661.
  7. ^Arias HR, Targowska-Duda KM, Feuerbach D, Jozwiak K (August 2015)."Coronaridine congeners inhibit human α3β4 nicotinic acetylcholine receptors by interacting with luminal and non-luminal sites".The International Journal of Biochemistry & Cell Biology.65:81–90.doi:10.1016/j.biocel.2015.05.015.PMID 26022277.
  8. ^"Ethnobotany & ethnopharmacology of Tabernaemontana divaricata".Free Online Library.
  9. ^Vieira IJ, Medeiros WL, Monnerat CS, Souza JJ, Mathias L, Braz-Filho R, et al. (September 2008)."Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures"(PDF).Anais da Academia Brasileira de Ciências.80 (3):419–426.doi:10.1590/s0001-37652008000300003.PMID 18797794.
  10. ^Krengel F, Mijangos MV, Reyes-Lezama M, Reyes-Chilpa R (July 2019). "Extraction and Conversion Studies of the Antiaddictive Alkaloids Coronaridine, Ibogamine, Voacangine, and Ibogaine from Two Mexican Tabernaemontana Species (Apocynaceae)".Chemistry & Biodiversity.16 (7) e1900175.doi:10.1002/cbdv.201900175.PMID 31095891.S2CID 157058497.
Drugs used in treatment ofdrug dependence (N07B)
Nicotine dependence
Alcohol dependence
Opioid dependence
Benzodiazepine dependence
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
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κ-opioid
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Tryptamines
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andesters/ethers
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Related compounds
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