Pheniramine

HCID 4761

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Basic information

CAS: 86-21-5
Standard SMILES: CN(C)CCC(c1ccccc1)c1ccccn1
InChIKey: IJHNSHDBIRRJRN-UHFFFAOYSA-N
Molecular formula: C16H20N2
Average molar mass: 240.34 g/mol
Monoisotopic mass: 240.16264865

Overview

N,N-dimethyl-3-phenyl-3-(2-pyridinyl)-1-propanamine is a member of pyridines and a tertiary amino compound.

Names & identifiers

Preferred name: Pheniramine
IUPAC: N,N-dimethyl-3-phenyl-3-pyridin-2-ylpropan-1-amine
English name: Pheniramine
Molecular formula: C16H20N2
Molecular weight: 240.34

Names & synonyms

pheniramineProphenpyridamineTripotonPyriton86-21-5PropheniramineFeniraminaPheniraminumdimethyl[3-phenyl-3-(pyridin-2-yl)propyl]amine2-(alpha-(2-Dimethylaminoethyl)benzyl)pyridineNSC-47965134FM9ZZ6M

Show more names

AVILMetronTrimetonFeniramineNCI-C60695PHENIRAMINE BASE

2-Pyridinepropanamine, N,N-dimethyl-gamma-phenyl-DTXSID0023454Pyridine, 2-(alpha-(2-(dimethylamino)ethyl)benzyl)-dimethyl(3-phenyl-3-(pyridin-2-yl)propyl)amine(+-)-PheniramineRefChem:860603DTXCID203454D04AA16

Database identifiers

CAS: 86-21-5
PubChem CID: 4761
DTXSID: DTXSID0023454
ChEMBL: CHEMBL1193
ChEBI: CHEBI:91591
UNII: 134FM9ZZ6M
EC Number: 201-656-2
Nikkaji: J4.935B

Properties

Computed structural properties

XLogP: 2.8
Topological polar surface area: 16.1 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 5
Heavy atoms: 18
Formal charge: 0
Complexity: 221

Experimental & physicochemical properties

DrugsPharmaceuticals -> Used in Switzerland

Solubility3.77e-01 g/L

Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan

Boiling Point175.00 °C. @ 25.00 mm Hg

Melting Point< 25 °C

Physical DescriptionSolid

Physicochemical properties

Melting point: 25 °C · <25 °C
Boiling point: 13 · bp13 181°; bp2 142°; bp0.5 135°
Density: 1.0081 · 1.0081
refractive index: 25 · nD25 1.5519 to 1.5521
Flash point: 9 ℃ · 9℃
storage temp.: -20 °C · -20°C
solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form: Oil
pka: 4.03 · pKa 4.03± 0.08;9.32± 0.06(H2O,t undefined,I=0.30(NaCl)) (Uncertain)
color: Colourless
Major Application: clinical testing
InChI: 1S/C16H20N2/c1-18(2)13-11-15(14-8-4-3-5-9-14)16-10-6-7-12-17-16/h3-10,12,15H,11,13H2,1-2H3
InChIKey: IJHNSHDBIRRJRN-UHFFFAOYSA-N
SMILES: CN(C)CCC(c1ccccc1)c2ccccn2
CAS DataBase Reference: 86 · 86-21-5(CAS DataBase Reference)
FDA UNII: 134 FM9ZZ6M · 134FM9ZZ6M
NIST Chemistry Reference: 2 · Pyridine, 2[alpha-(2-dimethyl aminoethyl)benzyl](86-21-5)
ATC code: 4 AA16,R06AB05 · D04AA16,R06AB05
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 2 · GHS02,GHS06,GHS08
Signal word: Danger
Hazard statements: 225 · H225-H301+H311+H331-H370
Precautionary statements: 210 · P210-P260-P280-P301+P310-P311
target organs: Eyes
Hazard Codes: F,T
Risk Statements: 11 · 11-23/24/25-39/23/24/25
Safety Statements: 16 · 16-36/37-45
RIDADR: 1230 · UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany: 1 · 1
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1

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 · 4 items

Danger

H300 (97.5%): Fatal if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information2-Pyridinepropanamine, N,N-dimethyl-.gamma.-phenyl-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 2-Pyridinepropanamine, N,N-dimethyl-.gamma.-phenyl-: Human health tier I assessment

Hazard Classes and CategoriesAcute Tox. 2 (97.5%)

Toxicology

Effects During Pregnancy and Lactation◈ What is pheniramine?

Safety data

wgk: 1
ridadr: UN1230 - class 3 - PG 2 - Methanol, solution
risk_code: 11-23/24/25-39/23/24/25
Signal word: Danger
Symbol(GHS): GHS02,GHS06,GHS08
hazard_code: F,T
safety_code: 16-36/37-45
Storage Class: 3 - Flammable liquids
target organs: Eyes
Hazard statements: H225-H301+H311+H331-H370
Hazard Classifications: Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
Precautionary statements: P210-P260-P280-P301+P310-P311

Chemistry & industry

Pharmacology

ATC Code · 4 items

R - Respiratory system

D - Dermatologicals

QD - Dermatologicals

QR - Respiratory system

PharmacodynamicsPheniramine acts as an antagonist to allergic symptoms stemming from inappropriate histamine release to reduce edema, itching, and redness. The same antihistamine effect also produces sedation by acting in the central nervous system.

Mechanism of Action · 1 item

Pheniramine competes with histamine for the histamine H1 receptor, acting as an inverse agonist once bound. The reduction in H1 receptor activity is responsible for reduced itching as well as reduced vasodilation and capillary leakage leading to less redness and edema. This can be seen in the suppression of the histamine-induced wheal (swelling) and flare (vasodilation) response. Inverse agonism of the H1 receptor in the CNS is also responsible for the sedation produced by first-generation antihistamines like pheniramine. The binding of pheniramine to H4 receptors, and subsequent inverse agonism, may also contribute to reduced itching by antagonizing inflammation.

Biological Half-LifeThe terminal half-life of pheniramine administered via IV is 8-17 h.

Metabolism/MetabolitesPheniramine undergoes N-dealkylation to N-didesmethylpheniramine and N-desmethylpheniramine.

MeSH Pharmacological Classification · 3 items

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

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.

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

Use Classification · 2 items

Pharmaceuticals -> Dermatologicals -> Antihistamines

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Applications

UsesPheniramine is an antigripal drug. Also, it is derived from 2-Benzylpyridine (B288740), which is a benzylpyridine with antifungal properties. 2-Benzylpyridine is also used as a chromogenic reagent for micro determination of Molybednum.

Upstream & downstream products

Upstream raw materials

Suppliers41 total

艾吉析科技（上海）有限公司17717235263 · [email protected]

广州佳途科技股份有限公司81960175-877 18933936954 · [email protected]

南京望知星医药科技有限公司18569809817 · [email protected]

上海科骊科生物技术有限公司021-34975789 18721102763 · [email protected]

Sinco Pharmachem (ShenZhen) R&D Co., Ltd.+86-18603013401 · [email protected]

Additional notes

DefinitionChEBI: N,N-dimethyl-3-phenyl-3-(2-pyridinyl)-1-propanamine is a tertiary amino compound and a member of pyridines.

Related reactions

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