(+)-Glaucine
Basic information
- CAS
475-81-0- Standard SMILES
COc1cc2c(cc1OC)-c1c(OC)c(OC)cc3c1[C@H](C2)N(C)CC3- InChIKey
RUZIUYOSRDWYQF-HNNXBMFYSA-N- Molecular formula
- C21H25NO4
- Average molar mass
- 355.4 g/mol
- Monoisotopic mass
- 355.17835828
Overview
(S)-glaucine is an aporphine alkaloid that is (S)-1,2,9,10-tetrahydroxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline in which the four phenolic hydrogens have been replaced by methyl groups. It has a role as an antibacterial agent, an antineoplastic agent, a platelet aggregation inhibitor, an antitussive, a muscle relaxant, a NF-kappaB inhibitor, a plant metabolite and a rat metabolite. It is an aporphine alkaloid, an organic heterotetracyclic compound, a polyether and a tertiary amino compound. It is a conjugate base of a (S)-glaucine(1+).
Names & identifiers
- Preferred name
- (+)-Glaucine
- IUPAC
- (6aS)-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
- English name
- Boldine dimethyl ether
- Molecular formula
- C21H25NO4
- Molecular weight
- 355.43
Names & synonyms
Glaucine475-81-0Bromcholitin(+)-Glaucine(6aS)-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolineNU19306XA7NSC-34396(6aS)-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo(de,g)quinolineRefChem:4080575,6,6a,7-Tetrahydro-1,2,9,10-tetramethoxy-6-methyl-4H-dibenzo(de,g)quinolined-GlaucineBoldine dimethyl ether
Show more names
Aids011385Aids-011385(S)-Glaucine
GlauventS-(+)-GlaucineGlaucine fumarate1,2,9,10-tetramethoxyaporphine1,2,9,10-Tetramethoxy-6a-alpha-aporphineNSC34396CHEMBL228082NSC 34396
Database identifiers
- CAS
475-81-0- PubChem CID
- 16754
- DTXSID
DTXSID8031100- ChEMBL
CHEMBL1788155、CHEMBL228082
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 40.2 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 489
Physicochemical properties
- Melting point
- 246 · 246-247℃
- alpha
- 20 · D20 +115° (c = 3 in alc)
- Boiling point
- 488.45 °C · 488.45°C (rough estimate)
- Density
- 1.166 · 1.166±0.06 g/cm3 (20 ºC 760 Torr)
- refractive index
- 1.5614 · 1.5614 (estimate)
- storage temp.
- -20 °C · -20°C Freezer, Under inert atmosphere
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 6.35 · 6.35±0.20(Predicted)
- color
- Pale Beige
- Cosmetics Ingredients Functions
- SKIN CONDITIONING
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 19306 XA7 · NU19306XA7
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H319-H315-H335
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
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 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H319-H315-H335
- Precautionary statements
- P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P-P264-P270-P301+P312-P330-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally.
Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS.
Applications
DescriptionGlaucine (Item No. 17338) is an analytical reference standard categorized as an antitussive. Glaucine has hallucinogenic properties. This product is intended for research and forensic applications.
Usesd-Glaucine has bronchodilator and antiinflammatory effects, acting as a PDE4 inhibitor and calcium channel blocker, and is used medically as an antitussive in some countries.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: (S)-glaucine is an aporphine alkaloid that is (S)-1,2,9,10-tetrahydroxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline in which the four phenolic hydrogens have been replaced by methyl groups. It has a role as a platelet aggregation inhibitor, a NF-kappaB inhibitor, an antitussive, an antibacterial agent, a muscle relaxant, an antineoplastic agent, a plant metabolite and a rat metabolite. It is an aporphine alkaloid, a polyether, an organic heterotetracyclic compound and a tertiary amino compound. It is a conjugate base of a (S)-glaucine(1+).
Related reactions
1 records
Compound notes
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