481-87-8

Basic information

• Product Name: IBOGAMINE
• Synonyms: 6,9-Methano-5H-pyrido[1',2':1,2]azepino[4,5-b]indole,ibogamine deriv.; (-)-Ibogamine;6,9-Methano-5H-pyrido[1',2':1,2]azepino[4,5-b]indole, 7-ethyl-6,6a,7,8,9,10,12,13-octahydro-,[6R-(6a,6ab,7b,9a)]-; Ibogamin; NSC 267705; [6R-(6a,6ab,7b,9a)]-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 NO: 481-87-8
• Molecular Formula: C19H24N2
• Molecular Weight: 280.40726
• Mol File: 481-87-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: 162-164 °C
• Boiling Point: 452.2°Cat760mmHg
• Flash Point: 227.3°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 2.28E-08mmHg at 25°C
• Refractive Index: 1.657
• PKA: 17.55±0.40(Predicted)
• CAS DataBase Reference: IBOGAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: IBOGAMINE(481-87-8)
• EPA Substance Registry System: IBOGAMINE(481-87-8)

Safety Data

• Hazardous Substances Data: 481-87-8(Hazardous Substances Data)

Usage

Uses

Ibogamine is used for treatment of movement-related disorders using noribogaine.

InChI:InChI=1/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?/m0/s1

Upstream product

• 19508-69-1 C₂₆H₂₈N₂O₄S 
• 19508-69-1 C₂₆H₂₈N₂O₄S 
• 81127-38-0 (1R,4S,7S)-7-Ethyl-6,6-dimethoxy-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid benzyl ester 
• 81127-33-5 (1R,4S,6S)-6-Ethyl-7-oxo-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid benzyl ester 
• 81127-22-2 ethyl 5-(2-ethylenedioxyethyl)-3-hydroxypiperidine-1-carboxylate 
• 81127-32-4 (1R,4S,7S)-7-Ethyl-2-aza-bicyclo[2.2.2]octan-6-one 
• 81127-29-9 benzyl (E)-9-(3-ethoxycarbonyl-2-propenyl)-1,4-dioxa-7-azaspiro<4.5>decane-7-carboxylate 
• 81127-27-7 benzyl (E)-5-(3-ethoxycarbonyl-2-propenyl)-3-oxopiperidine-1-carboxylate 
• 81127-24-4 benzyl 5-(1,3-dioxolan-2-ylmethyl)-3-hydroxypiperidine-1-carboxylate 
• 81127-26-6 benzyl (E)-5-(3-ethoxycarbonyl-2-propenyl)-3-hydroxypiperidine-1-carboxylate 
• 81127-28-8 benzyl 9-(2-oxoethyl)-1,4-dioxa-7-azaspiro<4.5>decane-7-carboxylate 
• 81127-25-5 benzyl 3-hydroxy-5-(2-oxoethyl)piperidine-1-carboxylate 
• 81127-23-3 5-[1,3]Dioxolan-2-ylmethyl-piperidin-3-ol 
• 50720-05-3 indolyl acetyl chloride 

Relevant articles and documents

IBOGAINE ANALOGS AS THERAPEUTICS FOR NEUROLOGICAL AND PSYCHIATRIC DISORDERS

The present invention provides a compound having the structure: formula wherein X1 is H or alkyl; Y1 is H, -alkyl, -alkenyl, -alkynyl, alkylaryl, -cycloalkyl, - aryl, heteroaryl, -alkyl-Y3 or -alkyl-C(O)Y4, and Y2 is H, -alkyl, -alkenyl, -alkynyl, alkylaryl, -cycloalkyl, - aryl, heteroaryl, -alkyl-Yg or -alkyl-C(O)Y4, wherein each Y3 is, independently, -OH, -O(alkyl), -NH2, - NH(alkyl) or halogen, and each Y4 is, independently, -OH, -O(alkyl), -NH2, -NH(alkyl) or -N(alkyl)2; Z1 is H, -alkyl, -alkenyl, -alkynyl, alkylaryl, -aryl, heteroaryl, -alkyl-Zg or -alkyl-C(O)Z4, and Z2 is H, -alkyl, -alkenyl, -alkynyl, alkylaryl, -aryl, heteroaryl, -alkyl-Zg or -alkyl-C(O)Z4, wherein each Z3 is, independently, -OH, -O(alkyl), -NH2, - NH(alkyl) or halogen, and each Z4 is, independently, -OH, -O(alkyl), -NH2, -NH(alkyl) or -N(alkyl)2; R1, R2, R3 and R4 are each, independently, -H, -F, -Cl, -Br, -I, -NO2, -CN, -CF3, -CF2H, -OCF3, -(alkyl), -(alkenyl), -(alkynyl), -(aryl), -(heteroaryl), -OH, -OAc, -O-(alkyl), -O-(alkenyl), - O-(alkynyl), -O-(aryl), -O-(heteroaryl), -SH, -S-(alkyl), S (alkenyl), -S-(alkynyl), -S-(aryl), -S-(heteroaryl), -NH2, -NH- (alkyl), -NH-(alkenyl), -NH-(alkynyl), -NH-(aryl), -NH- (heteroaryl), -C(0)R5, -S(O)R5, -SO2R5, -NHSO2R5, -0C(0)R5, SC(0)R5, -NHC(O)R6 or -NHC(S)R6, wherein each R5 is, independently, -(alkyl), -(aryl), (heteroaryl), -OH, -O(alkyl), -NH2, -NH(alkyl) or N(alkyl)2, and wherein each R6 is, independently, -(alkyl), -(aryl), -O- (alkyl), -S-(alkyl), -S-(aryl), -NH2, -NH(alkyl) or N(alkyl)2, wherein the compound is other than any of ibogaine, ibogamine, N- methyl-ibogaine, N-methyl-noribogaine, N-ethyl-noribogaine, N-methyl- ibogamine or 10-ethoxy-ibogamine, or a pharmaceutically acceptable salt of the compound, and methods of using the composition to treat pain, depressive disorders, mood disorders, anxiety disorders, substance use disorders, opioid use disorders, and opioid withdrawal symptoms.

Catalyzed asymmetric Diels - Alder reactions of benzoquinone. Total synthesis of (-)-ibogamine

The Diels - Alder reaction of 1,4-benzoquinone with 1,3-dienes catalyzed by Mikami's [Ti{(S)-binol(2 -)}Cl2] complex (binol = [1,1′-binaphthalene]-2,2′-diol) gives cycloadducts in good yield and in high enantiomer excess. A model is proposed to

A novel approach to iboga alkaloids: Total synthesis of (±)-ibogamine and (±)-epi-ibogamine

A novel approach to the total synthesis of (±)-ibogamine and (±)-epi-ibogamine, featuring electrophilic substitution at C(2) of N'-CBZ-tryptamine by an allylic acetate, is described.