Basic information
- CAS
532-12-7- Standard SMILES
c1cncc(C2=NCCC2)c1- InChIKey
DPNGWXJMIILTBS-UHFFFAOYSA-N- Molecular formula
- C9H10N2
- Average molar mass
- 146.19 g/mol
- Monoisotopic mass
- 146.08439833
Names & identifiers
- Preferred name
- Myosmine
- IUPAC
- 3-(3,4-dihydro-2H-pyrrol-5-yl)pyridine
- English name
- MYOSMINE
- Molecular formula
- C9H10N2
- Molecular weight
- 146.19
Names & synonyms
Myosmine532-12-73-(3,4-Dihydro-2H-pyrrol-5-yl)pyridine3-(1-Pyrrolin-2-yl)pyridine2-(3-Pyridyl)-1-pyrrolinePyridine, 3-(3,4-dihydro-2H-pyrrol-5-yl)-CHEBI:7051DTXSID708918669O0A545W4LRefChem:160358DTXCID001009059637-297-7
Show more names
NICOTINE RELATED COMPOUND DMYOSIMEyosmineMYSOMINEMyosmingBrn 0119254MYOSMINE(RG)
MFCD00052019MiosmineNicotine EP Impurity D3-(1-PYRROLIN-2-YL)-PYRIDINE3-(4,5-Dihydro-3H-pyrrol-2-yl)-pyridineCHEMBL4234293-(2-Pyrrolin-2-yl)pyridinePyridine, 3-(1-pyrrolin-2-yl)-
Database identifiers
- CAS
532-12-7- PubChem CID
- 442649
- DTXSID
DTXSID70891866- ChEMBL
CHEMBL423429- ChEBI
CHEBI:7051- UNII
- 9O0A545W4L
- EC Number
- 637-297-7
- Nikkaji
- J11.722F
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 25.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 163
Experimental & physicochemical properties
Melting Point40.5 - 42 °C
Physical DescriptionSolid
Kovats Retention Index1427.3
Collision Cross Section
128.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
130.49 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；127.92 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 42 · 42-44°C
- Boiling point
- 82 · 82-83°C 0,5mm
- Density
- 1.12 · 1.12±0.1 g/cm3(Predicted)
- Flash point
- 82 · 82-83°C/0.5mm
- storage temp.
- 2 · 2-8°C
- solubility
- Methanol (Slightly), Water (Sparingly)
- pka
- 1 · pK1:5.26 (25°C)
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]；H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (87.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 49 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory InformationStatus: Active Update: 24-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34234
Hazard Classes and CategoriesAcute Tox. 4 (100%)；Skin Irrit. 2 (100%)；Eye Irrit. 2 (100%)；STOT SE 3 (87.8%)
Regulatory information
Regulatory InformationStatus: Active Update: 24-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34234
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm；Extracellular
Applications
DescriptionThe alkaloids found in tobacco smoke may be separated into those which are volatile in steam and those which are non-volatile. Myosmine occurs in the former group and, although only present in small quantities, is the most fully investigated of these bases. The alkaloid is normally obtained as an oily liquid which may be crystallized. It is optically inactive and readily soluble in light petroleum or Et20. It forms a hydrochloride as a microcrystalline powder which, on sublimation yields colourless rods, m.p. ISS-8°C. The dihydrochloride, also a microcrystalline powder, yields colourless needles on sublimation, m.p. 1S0- 17 Soc. The base also furnishes a dipicrate, m.p. 182-3°C (dec.) and a dipi_x0002_crolonate, m.p. 204°C (dec.). On dehydrogenation it gives 2-(3'-pyridyl)-pyrrole (picrate, m.p. 200°C) identical with that obtained in a similar manner from nornicotine. According to Woodward and his colleagues, the alkaloid is one of several products formed when nicotine is dehydrogenated over prepared quartz at S70°C. It is readily hydrolyzed in H20 to yield 3-pyridyl-r-aminopropyl ketone, forming a crystalline phenylhydrazone, m.p. 20l-2°C.
Usesmitogen
UsesTobacco alkaloidReactant for:Nitrosation reactionsPeroxidation reaction with hydrogen peroxide
UsesMyosmine is an alkaloid found in tobacco. Myosmine has been suspected to be a tobacco-independent carcinogenic source.
Upstream & downstream products
Upstream raw materials
Related reactions
11 records
Compound notes
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