Myosmine

Names

[ CAS No. ]:
532-12-7

[ Name ]:
Myosmine

[Synonym ]:
Prestwick_202
3-(4,5-dihydro-3H-pyrrol-2-yl)-pyridine
Pyridine, 3-(1-pyrrolin-2-yl)-
dehydronornicotine
3-(3,4-Dihydro-2H-pyrrol-5-yl)pyridine
Pyridine, 3-(3,4-dihydro-2H-pyrrol-5-yl)-
MFCD00052019
3-(1-Pyrrolin-2-yl)pyridine
Myosmine
Pyridine,3-(3,4-dihydro-2H-pyrrol-5-yl)

Biological Activity

[Description]:

Myosmine, a specific tobacco alkaloid in nuts and nut products, has low affinity for a4b2 nicotinic acetylcholinergic receptors (nAChR) with a Ki of 3300 nM[1][2].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> nAChR

Signaling Pathways >> Neuronal Signaling >> nAChR

Research Areas >> Metabolic Disease

[Target]

Ki: 3300 nM (a4b2 nAChR) and >10 µM (AT1)[1]

[In Vitro]

Myosmine is easily nitrosated, yielding 4-hydroxy-1-(3-pyridyl)-1-butanone (HPB) and the esophageal tobacco carcinogen N'-nitrosonornicotine[2].

[In Vivo]

Myosmine (0.001, 0.005, 0.5, and 50 micromol/kg; oral; in Wistar rats) causes a higher percentage of the radioactivity excreted in urine (86.2% and 88.9%) at the two lower doses (0.001 and 0.005 micromol/kg),as compared with the higher doses (0.5 and 50 micromol/kg), where only 77.8% and 75.4% of the dose is found in urine[2].

[References]

[1]. G Ferretti, er al. Binding of Nicotine and Homoazanicotine Analogues at Neuronal Nicotinic Acetylcholinergic (nACh) Receptors. Bioorg Med Chem Lett. 2003 Feb 24;13(4):733-5.

[2]. Wolfgang Zwickenpflug, et al. Metabolism of Myosmine in Wistar Rats. Drug Metab Dispos. 2005 Nov;33(11):1648-56.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
244.7±22.0 °C at 760 mmHg

[ Melting Point ]:
42-44°C

[ Molecular Formula ]:
C₉H₁₀N₂

[ Molecular Weight ]:
146.189

[ Flash Point ]:
101.8±22.3 °C

[ Exact Mass ]:
146.084396

[ PSA ]:
25.25000

[ LogP ]:
-0.63

[ Vapour Pressure ]:
0.0±0.5 mmHg at 25°C

[ Index of Refraction ]:
1.611

[ Storage condition ]:
2-8°C

[ Stability ]:
Moisture, Temperature Sensitive

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UT7660000

CHEMICAL NAME :: Pyridine, 3-(1-pyrrolin-2-yl)-

CAS REGISTRY NUMBER :: 532-12-7

BEILSTEIN REFERENCE NO. :: 0119254

LAST UPDATED :: 199709

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C9-H10-N2

MOLECULAR WEIGHT :: 146.21

WISWESSER LINE NOTATION :: T6NJ C- BT5N AUTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1875 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 63,423,1946

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 190 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 63,423,1946

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

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

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UT7660000

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

A reversed-phase HPLC-UV method developed and validated for simultaneous quantification of six alkaloids from Nicotiana spp.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 997 , 142-5, (2015)

A reversed-phase HPLC-UV method was developed, optimized, and validated for the separation and quantitation of six target alkaloids from leaves of Nicotiana species (nicotine, nornicotine, anatabine, ...

Effects of nicotine and minor tobacco alkaloids on intracranial-self-stimulation in rats.

Drug Alcohol Depend. 153 , 330-4, (2015)

While nicotine is the primary addictive compound in tobacco, other tobacco constituents including minor alkaloids (e.g., nornicotine, anabasine) may also contribute to tobacco addiction by mimicking o...

Low-dose nicotine self-administration is reduced in adult male rats naïve to high doses of nicotine: implications for nicotine product standards.

Exp. Clin. Psychopharmacol. 22(5) , 453-9, (2014)

Product standards that greatly reduce the content of nicotine within cigarettes may result in improved public health. The study presented here used an animal model to investigate whether individuals w...