Conessine

Names

[ CAS No. ]:
546-06-5

[ Name ]:
Conessine

[Synonym ]:
3β-(Dimethylamino)con-5-enine
3-β-(Dimethylamino)con-5-enine
CONESSIN
Conessine
Con-5-enin-3-amine, N,N-dimethyl-, (3β)-
(3S,3aS,5aS,5bR,9S,11aR,11bS,13aR)-N,N,2,3,11a-Pentamethyl-2,3,3a,4,5,5a,5b,6,8,9,10,11,11a,11b,12,13-hexadecahydro-1H-naphtho[2',1':4,5]indeno[1,7a-c]pyrrol-9-amine
Konessin
ROGUESSINE
Conessine,N,N-Dimethyl-con-5-enin-3-amine
(3β)-N,N-Dimethylcon-5-enin-3-amine
ROQUESSINE
Wrightine
NERVINE
3β-(Dimethylamino)con-5-ene
(3b)-N,N-Dimethylcon-5-enin-3-amine
3b-(Dimethylamino)con-5-enine
Con-5-enine, 3β- (dimethylamino)-
NERIINE
Con-5-enine, 3-β-(dimethylamino)-
1-Deazaadenosine
5-CONENIN-3BETA-DIMETHYLAMINE

Biological Activity

[Description]:

Conessine, a steroidal alkaloid, is a potent and selective histamine H3 receptor antagonist with Kis of 5.4, 6.0, 5.7 and 25 nM for human, dog, guinea pig, and rat H H3 receptor, respectively. Anti-malarial activity[1].

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> Histamine Receptor

Research Areas >> Infection

Signaling Pathways >> GPCR/G Protein >> Histamine Receptor

[Target]

H3 Receptor:5.4 nM (Ki)

rat H3 receptor:25 nM (Ki)

Guinea pig H3 Receptor:6.0 nM (Ki)

Dog H3 Receptor:5.7 nM (Ki)

[References]

[1]. Santora VJ, et al. A new family of H3 receptor antagonists based on the natural product Conessine. Bioorg Med Chem Lett. 2008;18(4):1490-1494.

[2]. Kim H, et al. Conessine treatment reduces dexamethasone-induced muscle atrophy by regulating MuRF1 and atrogin-1 expression [published online ahead of print, 2018 Feb 1]. J Microbiol Biotechnol. 2018;10.4014.jmb.1711.11009.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
450.4±45.0 °C at 760 mmHg

[ Melting Point ]:
126-127ºC

[ Molecular Formula ]:
C₂₄H₄₀N₂

[ Molecular Weight ]:
356.588

[ Flash Point ]:
199.6±16.5 °C

[ Exact Mass ]:
356.319153

[ PSA ]:
6.48000

[ LogP ]:
5.71

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.564

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GK7621000

CHEMICAL NAME :: Con-5-enine, 3-beta-(dimethylamino)-

CAS REGISTRY NUMBER :: 546-06-5

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C24-H40-N2

MOLECULAR WEIGHT :: 356.66

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 208 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 58,373,1936

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 138 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 58,373,1936

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
GK7621000

Articles

[New orientation and new therapeutic weapons in the therapy of intestinal amebiasis].

Minerva Med. 43(59-60) , 129-33, (1952)

Highly enantioselective construction of fused pyrrolidine systems that contain a quaternary stereocenter: concise formal synthesis of (+)-conessine.

Angew. Chem. Int. Ed. Engl. 43(19) , 2543-6, (2004)

High-performance thin layer chromatography method for estimation of conessine in herbal extract and pharmaceutical dosage formulations.

J. Pharm. Biomed. Anal. 46(2) , 391-4, (2008)

A new, simple, sensitive, precise and robust high-performance thin layer chromatographic (HPTLC) method was developed for the estimation of conessine in herbal extracts and pharmaceutical dosage forms...