4H-Dibenzo[de,g]quinoline-10,11-diol, 5,6,6a,7-tetrahydro-6-methyl-, hydrochloride (1:1), (6aR)-

HCID 9410

Notes Reactions

Substructure search Find similar structures

Basic information

CAS: 314-19-2
Standard SMILES: CN1CCc2cccc3c2[C@H]1Cc1ccc(O)c(O)c1-3.Cl
InChIKey: SKYZYDSNJIOXRL-BTQNPOSSSA-N
Molecular formula: C17H18ClNO2
Average molar mass: 303.8 g/mol
Monoisotopic mass: 303.1026065

Names & identifiers

Preferred name: 4H-Dibenzo[de,g]quinoline-10,11-diol, 5,6,6a,7-tetrahydro-6-methyl-, hydrochloride (1:1), (6aR)-
IUPAC: (6aR)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol;hydrochloride
English name: Apomorphine hydrochloride
Molecular formula: C17H18ClNO2
Molecular weight: 303.78

Names & synonyms

(-)-Apomorphine hydrochloride4H-Dibenzo(de,g)quinoline-10,11-diol, 5,6,6a,7-tetrahydro-6-methyl-, hydrochloride (1:1), (6aR)-4H-Dibenzo[de,g]quinoline-10,11-diol, 5,6,6a,7-tetrahydro-6-methyl-, hydrochloride (1:1), (6aR)-RefChem:527368314-19-2(R)-(-)-Apomorphine hydrochlorideApomorphine chlorideApomorphinium chlorideApomorphine hydrochloride anhydrous(-)-Apomorphine (hydrochloride)9K13MD7A0DApomorphine.HCl

Show more names

APOMORPHINE HCLAPL-130277(?)-Apomorphine(r)-idUPRIMATAK251)KW-6500R(–)-APONSC 11442APL130277

R-(-)-Apomorphine hydrochlorideApomorphine SLBritajectNSC-11442Apomorphin hydrochloridpomorphini hydrochloridumApomorphinum hydrochloricum(6aR)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol;hydrochloride

Database identifiers

CAS: 314-19-2
PubChem CID: 9410
DTXSID: DTXSID5040598
UNII: 9K13MD7A0D

Properties

Computed structural properties

Topological polar surface area: 43.7 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 3
Rotatable bonds: 0
Heavy atoms: 21
Formal charge: 0
Complexity: 374

Experimental & physicochemical properties

Collision Cross Section161.7 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point: 250 ℃ · >250℃
storage temp.: Store at RT
solubility: 1.08 mg/mL · ≥1.08 mg/mL in EtOH with ultrasonic; ≥12.9 mg/mL in DMSO; ≥5.12 mg/mL in H2O
form: solid
FDA UNII: 9 K13MD7A0D · 9K13MD7A0D
EPA Substance Registry System: Apomorphine hydrochloride (314-19-2)
Protein binding: 90 % · 90%
Excreted unchanged in urine: 2 % · <2%
Volume of distribution: 2 · 2-19(L/kg)
Biological half-life: 29.1 · 29.1-36.9 minutes
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H334-H312-H332-H317
Precautionary statements: 264 · P264-P270-P301+P312-P330-P501-P261-P271-P304+P340-P312-P280-P302+P352-P312-P322-P363-P501-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P261-P285-P304+P341-P342+P311-P501
RIDADR: 3249 · 3249
TSCA: TSCA listed
HazardClass: 6.1 · 6.1(b)
PackingGroup: III
Toxicity: 20 mg/plate · mmo-sat 20 mg/plate MUREAV 137,17,84

Safety & regulation

Hazard information

Other Safety Information · 1 item

IMAP assessments - 4H-Dibenzo[de,g]quinoline-10,11-diol, 5,6,6a,7-tetrahydro-6-methyl-, hydrochloride, (R)-: Environment tier I assessment；IMAP assessments - 4H-Dibenzo[de,g]quinoline-10,11-diol, 5,6,6a,7-tetrahydro-6-methyl-, hydrochloride, (R)-: Human health tier I assessment

Safety data

tsca: TSCA listed
ridadr: 3249
Toxicity: mmo-sat 20 mg/plate MUREAV 137,17,84
Signal word: Warning
Symbol(GHS): GHS07
hazard_class: 6.1(b)
packing_group: III
Hazard statements: H302-H334-H312-H332-H317
Precautionary statements: P264-P270-P301+P312-P330-P501-P261-P271-P304+P340-P312-P280-P302+P352-P312-P322-P363-P501-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P261-P285-P304+P341-P342+P311-P501

Chemistry & industry

Uses & manufacturing

General Manufacturing Information4H-Dibenzo[de,g]quinoline-10,11-diol, 5,6,6a,7-tetrahydro-6-methyl-, hydrochloride (1:1), (6aR)-: INACTIVE

Applications · 3 items

UsesEmetic.

Uses(R)-(-)-Apomorphine Hydrochloride is a prototypical dopamine agonist. Potential treatment for Parkinson’s disease.

General DescriptionApomorphine hydrochloride,(6aR)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolone-10,11-diol hydrochloride (Apokyn), is awhite or off-white powder or crystal soluble in hot water(pKa＝8.92). Apormorphine is an aporphine alkaloid of thebenzoquinoline class. Oral apomorphine is poorly absorbedand has a bioavailability of less than 4%. Upon subcutaneousadministration, apomorphine is completely absorbed. Within10 to 20 minutes, the maximum concentration of the drug isdistributed from the blood plasma to the CSF. Other potentialroutes of administration include continuous subcutaneous infusion,intravenous infusion, intranasal spray application,sublingual, and rectal administration.23 The agent is highlylipophilic in nature, allowing for rapid diffusion across theBBB after injection. Apomorphine has a short plasma halflife;however, clinical effects may last from 60 to 90 minutes.Apomorphine displays a significant degree of interpatientvariability in its pharmacokinetic profile. Studies of bothintravenous and subcutaneous injection routes found this variation was not attributable to body weight, age, gender,and duration of PD or L-DOPA dose/duration alone.Apomorphine is extensively metabolized. Hypothesizedroutes include sulfation, N-demethylation, glucuronidation,and oxidation. Subcutaneous injections of apomorphine arerenally and hepatically cleared, with the majority appearingto be renally cleared. Dosage adjustments are needed in bothliver and renal impairment. The activity of apomorphine isbelieved to be caused by stimulation of postsynaptic D1- andD2-type receptors within the caudate/putamen in the brain.Apomorphine is indicated for the acute, intermittent treatmentof hypomobility, “off” episodes (“end-of-dose wearingoff” and unpredictable on/off episodes) associated with advancedPD.