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Ipidacrine

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Name

Ipidacrine

EINECS 676-166-9
CAS No. 62732-44-9 Density 1.17 g/cm3
PSA 38.91000 LogP 2.61250
Solubility N/A Melting Point 202-203 °C(Solv: methanol (67-56-1); water (7732-18-5))
Formula C12H16N2 Boiling Point 367.969 °C at 760 mmHg
Molecular Weight 188.272 Flash Point 203.991 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 62732-44-9 (2,3,5,6,7,8-HEXAHYDRO-1H-CYCLOPENTA[B]QUINOLIN-9-YLAMINE) Hazard Symbols IrritantXi
Synonyms

Neuromidine;2, 3, 5, 6, 7, 8-Hexahydro-1H-cyclopenta[b]quinolin-9-amine;

Article Data 5

Ipidacrine Synthetic route

diphosphorus pentaoxide (P2O0)

diphosphorus pentaoxide (P2O0)

78-40-0

triethyl phosphate

2941-23-3

2-amino-1-cyanocyclopentene

Conditions
ConditionsYield
With sodium hydroxide In methanol; ethanol; water; cyclohexanone; toluene91%
58996-10-4

4'-Oxo-spiropyrimidin>

Conditions
ConditionsYield
With trichlorophosphate In toluene for 24h; Heating;79%
With trichlorophosphate In toluene for 24h; Mechanism; Heating; other time; various ratio POCl3/educt;79%
108-94-1

cyclohexanone

2941-23-3

2-amino-1-cyanocyclopentene

Conditions
ConditionsYield
With zinc(II) chloride In xylene Heating;
74-88-4

methyl iodide

4-methyl-9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopentaquinoline iodide

Conditions
ConditionsYield
In methanol at 40℃;92%
79-04-9

chloroacetyl chloride

2-chloro-N-(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-yl)acetamide

Conditions
ConditionsYield
In chloroform at 0℃; for 1h; Reflux;2 g

N-(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-yl)-2-(4-(pyridin-2-yl)piperazin-1-yl)acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: chloroform / 1 h / 0 °C / Reflux
2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 150 °C
View Scheme

2-(4-benzo[1,3]dioxol-5-ylmethylpiperazin-1-yl)-N-(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-yl)acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: chloroform / 1 h / 0 °C / Reflux
2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 150 °C
View Scheme

N-(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-yl)-2-{4-[(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-ylcarbamoyl)methyl]piperazin-1-yl}acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: chloroform / 1 h / 0 °C / Reflux
2: potassium carbonate / N,N-dimethyl-formamide / 1150 °C
View Scheme

N-(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-yl)-2-(4-methylpiperazin-1-yl)acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: chloroform / 1 h / 0 °C / Reflux
2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 150 °C
View Scheme

4-[(2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-9-ylcarbamoyl)methyl]piperazine-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: chloroform / 1 h / 0 °C / Reflux
2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 150 °C
View Scheme

Ipidacrine Specification

The Ipidacrine, with the CAS registry number 62732-44-9, is also known as 2, 3, 5, 6, 7, 8-Hexahydro-1H-cyclopenta[b]quinolin-9-ylamine. This chemical's molecular formula is C12H16N2 and molecular weight is 188.27. What's more, its IUPAC name is 2, 3, 5, 6, 7, 8-Hexahydro-1H-cyclopenta[b]quinolin-9-amine. This chemical’s classification code is Drug / Therapeutic Agent. In addition, this chemical may cause inflammation to the skin or other mucous membranes.

Physical properties about Ipidacrine are: (1)ACD/LogP: 1.65; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 2; (8)#H bond donors: 2; (9)#Freely Rotating Bonds: 1; (10)Polar Surface Area: 38.91 Å2; (11)Index of Refraction: 1.634; (12)Molar Refractivity: 57.541 cm3; (13)Molar Volume: 160.858 cm3; (14)Polarizability: 22.811×10-24 cm3; (15)Surface Tension: 55.844 dyne/cm; (16)Density: 1.17 g/cm3; (17)Flash Point: 203.991 °C; (18)Enthalpy of Vaporization: 61.457 kJ/mol; (19)Boiling Point: 367.969 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: C1CCc2c(c(c3c(n2)CCC3)N)C1
(2) InChI: InChI=1/C12H16N2/c13-12-8-4-1-2-6-10(8)14-11-7-3-5-9(11)12/h1-7H2,(H2,13,14)
(3) InChIKey: YLUSMKAJIQOXPV-UHFFFAOYAA

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 39mg/kg (39mg/kg) SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE

BEHAVIORAL: TREMOR

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Pharmaceutical Chemistry Journal Vol. 11, Pg. 184, 1977.
mouse LD50 subcutaneous 52mg/kg (52mg/kg)   Pharmaceutical Chemistry Journal Vol. 23, Pg. 709, 1989.

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