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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H30N2O4.ClH
Molecular Weight 434.956
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHOLCODINE HYDROCHLORIDE

SMILES

Cl.CN1CC[C@]23[C@H]4OC5=C(OCCN6CCOCC6)C=CC(C[C@@H]1[C@@H]2C=C[C@@H]4O)=C35

InChI

InChIKey=ZOCXDCPBUWKMNA-RNFKYSJUSA-N
InChI=1S/C23H30N2O4.ClH/c1-24-7-6-23-16-3-4-18(26)22(23)29-21-19(5-2-15(20(21)23)14-17(16)24)28-13-10-25-8-11-27-12-9-25;/h2-5,16-18,22,26H,6-14H2,1H3;1H/t16-,17+,18-,22-,23-;/m0./s1

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C23H30N2O4
Molecular Weight 398.4953
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.phadia.com/Global/ImmunoCAP%20Allergens/Product%20Leaflets/Product_Leaflet_c261_Pholcodine.pdf http://www.ncbi.nlm.nih.gov/pubmed/23773349

Pholcodine is an opioid that has been widely used worldwide since 1950 for the treatment of non-productive cough in children and adults. Illicit drug. Additionally Pholcodine is a marker for sensitization to neuromuscular blocking agents (NMBA) and is intended for use as a diagnostic tool in NMBA-induced anaphylaxis.

CNS Activity

Originator

Chabrier, P. et al.
6
Sources: Chabrier, P., Guidicelli, R. & Thuillier, J. (1950) Etude chimique, pharmacologique et clinique d’un nouveau skdatif de la toux: la morpholyethyimorphine (M.E.M.). Annales Pharmaceutiques Francais. 8, 26 1-273.
Curator's Comment: Reference was retrieved from: http://onlinelibrary.wiley.com/doi/10.1111/j.1365-2710.1988.tb00502.x/epdf

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Mu-type opioid receptor
61
Target ID: P33535|||Q64064
Gene ID: 25601.0
Gene Symbol: Oprm1
Target Organism: Rattus norvegicus (Rat)
Agonist
2752
Mu-type opioid receptor
61
Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57
Gene ID: 4988.0
Gene Symbol: OPRM1
Target Organism: Homo sapiens (Human)
Agonist
2752
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Pholcodine Linctus B.P.

Approved Use

Cough
Diagnostic
Approved
8583
ImmunoCAP® Allergen c261

Approved Use

Anaphylaxis to neuromuscular blocking agents
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
9 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3741728/
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
14 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3741728/
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
27 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3741728/
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
50.7 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3741728/
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
57.1 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3741728/
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
12.8 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3190994/
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
26.3 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3190994/
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
47 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3741728/
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
91 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3741728/
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
162 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3741728/
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
933 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3741728/
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
929 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3741728/
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1004 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3741728/
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
0.72 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3190994/
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
2.91 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3190994/
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE saliva
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
6.61 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3190994/
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE saliva
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.67 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3190994/
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.97 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3190994/
20 mg 3 times / day multiple, oral
dose: 20 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PHOLCODINE saliva
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.55 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3190994/
20 mg 3 times / day multiple, oral
dose: 20 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PHOLCODINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
37 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3741728/
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
45.4 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3190994/
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
55.6 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3190994/
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE saliva
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
46.7 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3190994/
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE saliva
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
51.9 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3190994/
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHOLCODINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
53.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3190994/
20 mg 3 times / day multiple, oral
dose: 20 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PHOLCODINE saliva
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
10 mL 1 times / day multiple, oral
Studied dose
Dose: 10 mL, 1 times / day
Route: oral
Route: multiple
Dose: 10 mL, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17983379/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/17983379/
Sources:
https://pubmed.ncbi.nlm.nih.gov/17983379/
19.65 mg 3 times / day multiple, oral
Studied dose
Dose: 19.65 mg, 3 times / day
Route: oral
Route: multiple
Dose: 19.65 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17154678/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/17154678/
Disc. AE: Upper abdominal pain...
AEs leading to
discontinuation/dose reduction:
Upper abdominal pain (1.6%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/17154678/
20 mg 1 times / 8 hours multiple, oral
Studied dose
Dose: 20 mg, 1 times / 8 hours
Route: oral
Route: multiple
Dose: 20 mg, 1 times / 8 hours
Sources:
https://pubmed.ncbi.nlm.nih.gov/3190994/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/3190994/
Sources:
https://pubmed.ncbi.nlm.nih.gov/3190994/
AEs

AEs

AESignificanceDosePopulation
Upper abdominal pain 1.6%
Disc. AE
19.65 mg 3 times / day multiple, oral
Studied dose
Dose: 19.65 mg, 3 times / day
Route: oral
Route: multiple
Dose: 19.65 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17154678/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/17154678/
PubMed

PubMed

TitleDatePubMed
Clinical expert guidelines for the management of cough in lung cancer: report of a UK task group on cough.
2010-10-06
National pholcodine consumption and prevalence of IgE-sensitization: a multicentre study.
2010-04
[Anaphylaxis during anaesthesia].
2010-03-11
Cholinergic and oxidative stress mechanisms in sudden infant death syndrome.
2009-11
The pholcodine story.
2009-08
Pholcodine caused anaphylaxis in Sweden 30 years ago.
2009-05
On the origin and specificity of antibodies to neuromuscular blocking (muscle relaxant) drugs: an immunochemical perspective.
2009-03
Determination of opiates and cocaine in urine by high pH mobile phase reversed phase UPLC-MS/MS.
2009-02-01
Suspected anaphylactic reactions associated with anaesthesia.
2009-02
IgE-mediated anaphylactic reactions to neuromuscular blocking agents: can they be prevented?
2008-09
Determining plasma morphine levels using GC-MS after solid phase extraction to monitor drug levels in the postoperative period.
2008-06
Hypersensitivity reactions to neuromuscular blocking agents.
2008
Pholcodine exposure raises serum IgE in patients with previous anaphylaxis to neuromuscular blocking agents.
2007-12
Immunoglobulin E antibodies to rocuronium: a new diagnostic tool.
2007-08
Site-specific acid-base properties of pholcodine and related compounds.
2006-11
Pholcodine stimulates a dramatic increase of IgE in IgE-sensitized individuals. A pilot study.
2006-01
Comparative efficacy and tolerability of pholcodine and dextromethorphan in the management of patients with acute, non-productive cough : a randomized, double-blind, multicenter study.
2006
Automated multiple development thin-layer chromatography for separation of opiate alkaloids and derivatives.
2005-07-08
Validated toxicological determination of 30 drugs of abuse as optimized derivatives in oral fluid by long column fast gas chromatography/electron impact mass spectrometry.
2005-06
Prevalence of IgE antibodies to morphine. Relation to the high and low incidences of NMBA anaphylaxis in Norway and Sweden, respectively.
2005-04
Allergy to pholcodine: first case documented by oral challenge.
2005-04
Evaluation of the One-Step ELISA kit for the detection of buprenorphine in urine, blood, and hair specimens.
2004-07-16
The toxicity of opiates and their metabolites in HepG2 cells.
2003-10-25
Enzyme immunoassay validation for the detection of buprenorphine in urine.
2003-03
Comparative biotransformation of morphine, codeine and pholcodine in rat hepatocytes: identification of a novel metabolite of pholcodine.
2002-12
Interpretation of GC-MS opiate results in the presence of pholcodine.
2002-06-25
Impurity profiling of pholcodine by liquid chromatography electrospray ionization mass spectrometry (LC-ESI-MS).
2002-01
Comparison of eight commercial on-site screening devices for drugs-of-abuse testing.
2001-07
Angle closure risk from proprietary medicines.
2001-04

Sample Use Guides

In Vivo Use Guide
Syrup (1mg/ml pholcodine) Two 5 ml spoonfuls 3 or 4 times a day
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 20:58:20 GMT 2025
Edited
by admin
on Mon Mar 31 20:58:20 GMT 2025
Record UNII
42A8DMU44P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHOLCODINE, MONOHYDROCHLORIDE
Preferred Name English
PHOLCODINE HYDROCHLORIDE
Common Name English
MORPHINAN-6-OL, 7,8-DIDEHYDRO-4,5-EPOXY-17-METHYL-3-(2-(4-MORPHOLINYL)ETHOXY)-, MONOHYDROCHLORIDE, (5.ALPHA.,6.ALPHA.)-
Systematic Name English
Code System Code Type Description
FDA UNII
42A8DMU44P
Created by admin on Mon Mar 31 20:58:20 GMT 2025 , Edited by admin on Mon Mar 31 20:58:20 GMT 2025
PRIMARY
CAS
36418-24-3
Created by admin on Mon Mar 31 20:58:20 GMT 2025 , Edited by admin on Mon Mar 31 20:58:20 GMT 2025
PRIMARY
PUBCHEM
129722485
Created by admin on Mon Mar 31 20:58:20 GMT 2025 , Edited by admin on Mon Mar 31 20:58:20 GMT 2025
PRIMARY
Related Record Type Details
Structure of PHOLCODINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of PHOLCODINE
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