CAS 57574-09-1|CAS 30272-08-3|N-(6-carboxyhexyl)tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-aminium chloride|Amineptine|Amineptine hydrochloride|Survector|Maneon|N-(6-carboxyhexyl...

General Information

Structure

Molecular Formula

C₂₂H₂₈ClNO₂

Molecular Mass

373.91622

Exact Mass

373.18085682

Charge

0

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

Canonic Smiles

OC(=O)CCCCCC[NH2+]C1c2ccccc2CCc2c1cccc2.[Cl-]

Isomeric Smiles

[Cl-].OC(=O)CCCCCC[NH2+]C1c2c(CCc3c1cccc3)cccc2

Calculated Properties

JChem

LogD (pH = 7.4)

2.74

LogD (pH = 5.5)

2.72

Log P

2.74

Rotatable Bonds

8

H Donor

2

H Acceptors

2

Lipinski's Rule of Five

true

Acid pKa

4.41

Polar Surface Area

53.91

Polarizability

39.99

Molar Refractivity

112.63

LOG S

-4.69

Data Source

Academic Data

Data Source

Names and Identifiers

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 N-(6-carboxyhexyl)tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-aminium chloride

Synonyms

AmineptineAmineptine hydrochloride7-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylamino)heptanoic acid hydrochlorideamineptine hydrochloride

Brand Name

SurvectorManeon

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 N-(6-carboxyhexyl)tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-aminium chloride

Names and Identifiers

Registration numbers

PubChem SID

4650901216096781249742801

CAS Number

PubChem CID

ACToR Database

SureChEMBL Database

Beilstein Number

CHEBI ID

CHEMBL

Registration numbers

Properties

No Data Available

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Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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illicit; withdrawn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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• 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

• 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

• Grupper C: [New iatrogenic acne: acne caused by amineptin (Survector)] Ann Dermatol Venereol. 1988;115(11):1174-6. Pubmed

• Teillac D, Weber MJ, Lowenstein W, de Prost Y: [Acne caused by Survector] Ann Dermatol Venereol. 1988;115(11):1183-4. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:4380