N-(6-carboxyhexyl)tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-aminium chloride

• ChemBase ID: 4380
• Molecular Formular: C22H28ClNO2
• Molecular Mass: 373.91622
• Monoisotopic Mass: 373.18085682
• SMILES: [Cl-].OC(=O)CCCCCC[NH2+]C1c2c(CCc3c1cccc3)cccc2
• Canonical SMILES: OC(=O)CCCCCC[NH2+]C1c2ccccc2CCc2c1cccc2.[Cl-]
• InChI: InChI=1S/C22H27NO2.ClH/c24-21(25)13-3-1-2-8-16-23-22-19-11-6-4-9-17(19)14-15-18-10-5-7-12-20(18)22;/h4-7,9-12,22-23H,1-3,8,13-16H2,(H,24,25);1H
• InChIKey: VDPUXONTAVMIKZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(6-carboxyhexyl)tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-aminium chloride
• IUPAC Traditional name: N-(6-carboxyhexyl)tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-aminium chloride
• Brand Name: Maneon; Survector
• Synonyms: Amineptine hydrochloride; Amineptine

Database IDs

• CAS Number: 57574-09-1
• PubChem SID: 46509012; 160967812
• PubChem CID: 34869

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.41307
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.717727
• LogD (pH = 7.4): 2.742191
• Log P: 2.7436762
• Molar Refractivity: 112.6259 cm^3
• Polarizability: 39.421856 Å^3
• Polar Surface Area: 53.91 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.99
• LOG S: -7.31
• Solubility (Water): 1.84e-05 g/l

DETAILS

DrugBank - DB04836

• Drug Groups: illicit; withdrawn
• Description: The Food and Drug Administration suspended the marketing authorisation for Survector in 1999 and France withdrew it from the market, however several developing countries continued to produce it up until 2005.
• Indication: For the treatment of depression.
• Pharmacology: Amineptine is an atypical tricyclic antidepressant.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Half Life: 48 minutes for the parent drug and 2.5 hours for the metabolites.
• References: Vaugeois JM, Corera AT, Deslandes A, Costentin J: Although chemically related to amineptine, the antidepressant tianeptine is not a dopamine uptake inhibitor. Pharmacol Biochem Behav. 1999 Jun;63(2):285-90. [Pubmed] ; Grupper C: [New iatrogenic acne: acne caused by amineptin (Survector)] Ann Dermatol Venereol. 1988;115(11):1174-6. [Pubmed] ; Thioly-Bensoussan D, Charpentier A, Triller R, Thioly F, Blanchet P, Tricoire N, Noury JY, Grupper C: [Iatrogenic acne caused by amineptin (Survector). Apropos of 8 cases] Ann Dermatol Venereol. 1988;115(11):1177-80. [Pubmed] ; Vexiau P, Gourmel B, Husson C, Castot A, Rybojad M, Julien R, Fiet J, Puissant A, Cathelineau G: [Severe lesions of acne type induced by chronic amineptin poisoning: apropos of 6 cases] Ann Dermatol Venereol. 1988;115(11):1180-2. [Pubmed] ; Teillac D, Weber MJ, Lowenstein W, de Prost Y: [Acne caused by Survector] Ann Dermatol Venereol. 1988;115(11):1183-4. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Vaugeois JM, Corera AT, Deslandes A, Costentin J: Although chemically related to amineptine, the antidepressant tianeptine is not a dopamine uptake inhibitor. Pharmacol Biochem Behav. 1999 Jun;63(2):285-90. Pubmed
• Grupper C: [New iatrogenic acne: acne caused by amineptin (Survector)] Ann Dermatol Venereol. 1988;115(11):1174-6. Pubmed
• Thioly-Bensoussan D, Charpentier A, Triller R, Thioly F, Blanchet P, Tricoire N, Noury JY, Grupper C: [Iatrogenic acne caused by amineptin (Survector). Apropos of 8 cases] Ann Dermatol Venereol. 1988;115(11):1177-80. Pubmed
• Vexiau P, Gourmel B, Husson C, Castot A, Rybojad M, Julien R, Fiet J, Puissant A, Cathelineau G: [Severe lesions of acne type induced by chronic amineptin poisoning: apropos of 6 cases] Ann Dermatol Venereol. 1988;115(11):1180-2. Pubmed
• Teillac D, Weber MJ, Lowenstein W, de Prost Y: [Acne caused by Survector] Ann Dermatol Venereol. 1988;115(11):1183-4. Pubmed