Dihydrocodeine
Basic information
- CAS
125-28-0- Standard SMILES
COc1ccc2c3c1O[C@H]1[C@@H](O)CC[C@H]4[C@@H](C2)N(C)CC[C@@]341- InChIKey
RBOXVHNMENFORY-DNJOTXNNSA-N- Molecular formula
- C18H23NO3
- Average molar mass
- 301.4 g/mol
- Monoisotopic mass
- 301.1677936
Overview
Dihydrocodeine is a morphinane alkaloid.
Names & identifiers
- Preferred name
- Dihydrocodeine
- IUPAC
- (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
Names & synonyms
DIHYDROCODEINERapacodinNovicondinCodhydrineDehacodinHydrocodeine8,14-DihydroneopineDihidrocodeinaDihydroneopineCohydrinalpha-Hydrocodol125-28-0
Show more names
DrocodeDihydrocodeinumDiidrocodeinaRemedacenDH-codeineN9I9HDB855IDS-ND-008(SECT.2)NSC-231319
Database identifiers
- CAS
125-28-0- PubChem CID
- 5284543
- DTXSID
DTXSID5022936- ChEMBL
CHEMBL1595- ChEBI
CHEBI:135276- UNII
- N9I9HDB855
- EC Number
- 204-732-3
- Nikkaji
- J5.368F
Properties
Computed structural properties
- XLogP
- 2.2
- Topological polar surface area
- 41.9 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 471
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Narcotic Analgesics
DEA Schedule II Controlled Substance -> Opiates
Pharmaceuticals -> Used in Switzerland
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Pharmaceuticals -> Listed in ZINC15
Human Drugs
Breast Feeding; Lactation; Milk, Human; Analgesics, Opioid; Narcotics; Antitussive Agents
Pharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
Dissociation Constants8.75
Collision Cross Section168.6 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
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
Danger
H301+H311+H331 (90.7%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P233, P260, P261, P262, P264, P270, P271, P272, P280, P284, P301+P316, P302+P352, P304+P340, P316, P321, P330, P333+P317, P342+P316, P361+P364, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 43 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
DEA schedule II controlled substance
REACH registered substance: Dihydrocodeine (EC: 204-732-3)
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Dihydrocodeine
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
EPA Human Health Benchmarks for Pharmaceuticals
Dihydrocodeine
3.7
15.8
Dihydrocodeine bitartrate is given in combination with acetaminophen and caffeine in a capsule (as Trezix), with 16 mg dihydrocodeine bitartrate per capsule. The usual adult dosage is 2 Trezix capsules orally every 4 hours, as needed. No more than 5 doses, or 10 capsules should be taken in a 24-hour period.
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
PharmacodynamicsPossible opioid related side effects include, but are not limited to, drowsiness, nausea, headache, dry mouth, constipation, difficulty passing urine, and mild euphoria.
Mechanism of ActionDihydrocodeine is metabolized to dihydromorphine -- a highly active metabolite with a high affinity for mu opioid receptors. [3]
Biological Half-Life4h
Metabolism/Metabolites
Metabolized in the liver by CYP 2D6 into an active metabolite, dihydromorphine, and by CYP 3A4 into secondary primary metabolite, nordihydrocodeine. A third primary metabolite is dihydrocodeine-6-glucuronide. [1] The time for mean peak concentration in acid metabolites is 1.76h and 1.98h for a 30 and 60mg dose, respectively. The concentrations achieved were 563 ug/1 and 1476 ug/1, respectively. [2]
Dihydrocodeine has known human metabolites that include Desmethyl dihydrocodeine and Paramorfan.
FDA Pharmacological Classification
N9I9HDB855
DIHYDROCODEINE
Mechanisms of Action [MoA] - Full Opioid Agonists
Established Pharmacologic Class [EPC] - Opioid Agonist
Dihydrocodeine is an Opioid Agonist. The mechanism of action of dihydrocodeine is as a Full Opioid Agonist.
MeSH Pharmacological ClassificationCompounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS.
Absorption, Distribution and Excretion
Bioavailability is low (approximately 20%) if administered orally. This may be due to poor gastrointestinal absorption. It is also likely due to pre-systemic metabolism by the liver and intestinal wall. [2] The AUCs after oral and intravenous administration are similar (3203ug/l/h and 3401ug/l/h, respectively). [2] Time to peak values are 1.6 and 1.8hours for a 30mg and 60mg dose, respectively. The concentrations achieved were 71.8 ug/1 and 146 ug/1, respectively. [2]
Suppliers
Loading…
Open inquiries
Loading…
Related reactions
3 records
Compound notes
Loading…