Pseudoephedrine Hydrochloride

HCID 9581CAS 345-78-8

Basic information

Standard SMILES
CN[C@@H](C)[C@@H](O)c1ccccc1.Cl
InChIKey
BALXUFOVQVENIU-KXNXZCPBSA-N
Molecular formula
C10H16ClNO
Average molar mass
201.69 g/mol
Monoisotopic mass
201.0920418

Names & identifiers

Preferred name
Pseudoephedrine Hydrochloride
IUPAC
(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol;hydrochloride

Names & synonyms

PSEUDOEPHEDRINE HYDROCHLORIDEPseudoephedrine Hcl345-78-8RhinalairOtrinolNovafedd-Pseudoephedrine hydrochlorideSudafed 12 HourGalsudSudafed PlusSudafed 24 HourEfidac 24
Show more names
L(+)-Pseudoephedrine hydrochloride6V9V2RYJ8NNSC-33634Topcare 12 hour decongestantNSC-106567GALPSEUDD-(alpha-(1-Methylamino)ethyl)benzyl alcohol hydrochlorideDTXSID10889343

Database identifiers

CAS
345-78-8
PubChem CID
9581
DTXSID
DTXSID10889343
ChEMBL
CHEMBL1200724
UNII
6V9V2RYJ8N
EC Number
206-462-1

Properties

Computed structural properties

Topological polar surface area
32.3 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
2
Rotatable bonds
3
Heavy atoms
13

Experimental & physicochemical properties

Collision Cross Section132.1 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral];H315 (17.2%): Causes skin irritation [Warning Skin corrosion/irritation];H317 (73.9%): May cause an allergic skin reaction [Warning Sensitization, Skin];H319 (17.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (46%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 261 reports by companies from 24 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 Information · 2 items

Status: Active Update: 17-06-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/12556

Pseudoephedrine hydrochloride: Does not have an individual approval but may be used under an appropriate group standard

Other Safety Information · 1 item

IMAP assessments - Benzenemethanol, .alpha.-[1-(methylamino)ethyl]-,hydrochloride, [S-(R*,R*)]-: Environment tier I assessment;IMAP assessments - Benzenemethanol, .alpha.-[1-(methylamino)ethyl]-,hydrochloride, [S-(R*,R*)]-: Human health tier I assessment

Hazard Classes and CategoriesAcute Tox. 4 (100%);Skin Irrit. 2 (17.2%);Skin Sens. 1 (73.9%);Eye Irrit. 2 (17.2%);STOT SE 3 (46%)

Toxicology

Exposure RoutesPseudoephedrine is readily and almost completely absorbed from the GI tract and there is no evidence of first-pass metabolism.
Toxicity Summary · 1 item

Pseudoephedrine acts directly on both alpha- and, to a lesser degree, beta-adrenergic receptors. Through direct action on alpha-adrenergic receptors in the mucosa of the respiratory tract, pseudoephedrine produces vasoconstriction. Pseudoephedrine relaxes bronchial smooth muscle by stimulating beta2-adrenergic receptors. Like ephedrine, pseudoephedrine releasing norepinephrine from its storage sites, an indirect effect. This is its main and direct mechanism of action. The displaced noradrenaline is released into the neuronal synapse where it is free to activate the postsynaptic adrenergic receptors.

Signs and Symptoms · 1 item

Common adverse reactions include nervousness, restlessness, and insomnia. Rare adverse reactions include difficult/painful urination, dizziness/lightheadedness, heart palpitations, headache, increased sweating, nausea/vomiting, trembling, troubled breathing, unusual paleness, and weakness.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Pseudoephedrine hydrochloride

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

Regulatory information

Regulatory Information · 2 items

Status: Active Update: 17-06-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/12556

Pseudoephedrine hydrochloride: Does not have an individual approval but may be used under an appropriate group standard

Chemistry & industry

Pharmacology

Metabolism/MetabolitesHepatic. Half Life: 9-16 hours
FDA Pharmacological Classification · 4 items

PSEUDOEPHEDRINE HCL

Adrenergic alpha-Agonists [MoA]; alpha-Adrenergic Agonist [EPC]

PSEUDOEPHEDRINE HYDROCHLORIDE

alpha-Adrenergic Agonist [EPC]; Adrenergic alpha-Agonists [MoA]

MeSH Pharmacological Classification · 5 items

Agents, usually topical, that relieve itching (pruritus).

Agents that cause an increase in the expansion of a bronchus or bronchial tubes.

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood.

Drugs designed to treat inflammation of the nasal passages, generally the result of an infection (more often than not the common cold) or an allergy related condition, e.g., hay fever. The inflammation involves swelling of the mucous membrane that lines the nasal passages and results in inordinate mucus production. The primary class of nasal decongestants are vasoconstrictor agents. (From PharmAssist, The Family Guide to Health and Medicine, 1993)

Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475)

Uses & manufacturing

Uses · 1 item

For the treatment of nasal congestion, sinus congestion, Eustachian tube congestion, and vasomotor rhinitis, and as an adjunct to other agents in the optimum treatment of allergic rhinitis, croup, sinusitis, otitis media, and tracheobronchitis. Also used as first-line therapy of priapism.

General Manufacturing InformationBenzenemethanol, .alpha.-[(1S)-1-(methylamino)ethyl]-, hydrochloride (1:1), (.alpha.S)-: ACTIVE

Related reactions

8 records

Linked notes

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