Ibogaline

Ibogaline
Names
	IUPAC name (1R,17S)-17-Ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene
	Other names 12,13-Dimethoxyibogamine
Identifiers
CAS Number	482-18-8;
3D model (JSmol)	Interactive image;
ChemSpider	167742 ;
PubChem CID	193302;
CompTox Dashboard (EPA)	DTXSID70964024 ;
	InChI InChI=1S/C18H21ClN2/c19-17-7-4-8-18(15-17)21-13-11-20(12-14-21)10-9-16-5-2-1-3-6-16/h1-8,15H,9-14H2 Key: NKMGWZZAFWDLFG-UHFFFAOYSA-N;
	SMILES CC[C@H]1C[C@@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=CC(=C(C=C45)OC)OC;
Properties
Chemical formula	C21H28N2O2
Molar mass	340.467 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Ibogaline is an alkaloid found in Tabernanthe iboga along with the related chemical compounds ibogaine, ibogamine, and other minor alkaloids. It is a relatively smaller component of Tabernanthe iboga root bark total alkaloids (TA) content. The percentage of ibogaline in T. iboga root bark is up to 15% TA with ibogaine constituting 80% of the alkaloids and ibogamine up to 5%.[1][2]

In rodents, ibogaline induces more body tremor and ataxia compared to ibogaine and ibogamine.[3] Among a series of iboga and harmala alkaloids evaluated in rats, the study authors found the following order of potency in causing tremors:[3]

ED₅₀ (μmol/kg, sc): tabernanthine (4.5) > ibogaline (7.6) > harmaline (12.8) > harmine (13.7) > ibogaine (34.8) > noribogaine (176.0)

A subsequent study confirmed these findings.[4]

References

Piotr Popik, Phil Skolnick (1998). Pharmacology of Ibogaine and Ibogaine-Related Alkaloids. The Alkaloids. 52. San Diego.
Norbert Neuss (1959). "Notes- Alkaloids from Apocynaceae II. Ibogaline, A New Alkaloid From Tabernanthe Iboga Baill". J. Org. Chem. 24 (12): 2047–2048. doi:10.1021/jo01094a622.
Zetler G, Singbartl G, Schlosser L (1972). "Cerebral Phamacokinetics of Tremor-producing Harmala and Iboga Alkaloids". Pharmacology. 7 (4): 237–248. doi:10.1159/000136294. PMID 5077309.
Glick SD, Kuehne ME, Raucci J, Wilson TE, Larson D, Keller RW Jr, Carlson JN (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 Res. 657 (1–2): 14–22. doi:10.1016/0006-8993(94)90948-2. PMID 7820611.

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[1] Piotr Popik, Phil Skolnick (1998). Pharmacology of Ibogaine and Ibogaine-Related Alkaloids. The Alkaloids. 52. San Diego.

[2] Norbert Neuss (1959). "Notes- Alkaloids from Apocynaceae II. Ibogaline, A New Alkaloid From Tabernanthe Iboga Baill". J. Org. Chem. 24 (12): 2047–2048. doi:10.1021/jo01094a622.

[ref4-3] Zetler G, Singbartl G, Schlosser L (1972). "Cerebral Phamacokinetics of Tremor-producing Harmala and Iboga Alkaloids". Pharmacology. 7 (4): 237–248. doi:10.1159/000136294. PMID 5077309.

[4] Glick SD, Kuehne ME, Raucci J, Wilson TE, Larson D, Keller RW Jr, Carlson JN (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 Res. 657 (1–2): 14–22. doi:10.1016/0006-8993(94)90948-2. PMID 7820611.

Ibogaline

See also

References