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Tripelennamine

HCID 5587
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
91-81-6
Standard SMILES
CN(C)CCN(Cc1ccccc1)c1ccccn1
InChIKey
UFLGIAIHIAPJJC-UHFFFAOYSA-N
Molecular formula
C16H21N3
Average molar mass
255.36 g/mol
Monoisotopic mass
255.17354768

Overview

Tripelenamine is an oily liquid with an amine odor. (NTP, 1992)

Names & identifiers

Preferred name
Tripelennamine
IUPAC
N'-benzyl-N,N-dimethyl-N'-pyridin-2-ylethane-1,2-diamine
English name
Tripelennamine
Molecular formula
C16H21N3
Molecular weight
255.36

Names & synonyms

tripelennamine91-81-6Pyrinamine baseTripelennaminBenzoxaleResistamineCizaronTonarilPiribenzilTripelennaminaPyribenzaminTripelenamina
Show more names
PYRIBENZAMINETripelenamineTripelennamine USP/EP/BPTripelennamine 1000 μg/mL in AcetonitrileN'-benzyl-N,N-dimethyl-N'-pyridin-2-ylethane-1,2-diamine1,2-Ethanediamine, N,N-dimethyl-N-(phenylmethyl)-N-2-pyridinyl-
TripelennaminumN-benzyl-N-[2-(dimethylamino)ethyl]pyridin-2-amine1,2-Ethanediamine, N,N-dimethyl-N'-(phenylmethyl)-N'-2-pyridinyl-2-(Benzyl(2-dimethylaminoethyl)amino)pyridineN-Benzyl-N',N'-dimethyl-N-2-pyridylethylenediaminebeta-Dimethylaminoethyl-2-pyridylbenzylaminebeta-Dimethylaminoethyl-2-pyridylaminotoluene3C5ORO99TY

Database identifiers

CAS
91-81-6
PubChem CID
5587
DTXSID
DTXSID8023717
ChEMBL
CHEMBL1241
ChEBI
CHEBI:9741

Properties

Computed structural properties

XLogP
3.3
Topological polar surface area
19.4 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
6
Heavy atoms
19
Formal charge
0
Complexity
236

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

LogP · 2 items

3.3

2.65

OdorAMINE ODOR
Color/FormYELLOW OIL
Solubility · 4 items

Very soluble (NTP, 1992)

1 G DISSOLVES IN: 0.77 ML WATER, 6 ML ALCOHOL, 6 ML CHLOROFORM, ABOUT 350 ML ACETONE; PRACTICALLY INSOL IN BENZENE, ETHER, ETHYL ACETATE /HYDROCHLORIDE/

MISCIBLE WITH WATER

2.84e+00 g/L

Human Drugs · 2 items

Breast Feeding; Lactation; Milk, Human; Antihistamines

Pharmaceuticals

Boiling Point · 2 items

365 to 374 °F at 1.7 mmHg (NTP, 1992)

19.3-20.5 °C @ 5 mm Hg

Refractive IndexINDEX OF REFRACTION: 1.5759-1.5765 @ 25 °C/D
Physical Description · 2 items

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

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 24 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationTripelennamine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - 1,2-Ethanediamine, N,N-dimethyl-N'-(phenylmethyl)-N'-2-pyridinyl-: Human health tier I assessment
Fire HazardsFlash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Health Hazards · 1 item

SYMPTOMS: Symptoms of exposure to this compound may include euphoria, aplastic anemia, excitement, hallucinations, ataxia, incoordination, athetosis, convulsions, postictal depression, dry mouth, fixed dilated pupils, flushing of the face, fever, central nervous system depression, drowsiness and coma. (NTP, 1992)

FDA Requirements · 1 item

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Chemistry & industry

Pharmacology

ATC Code · 4 items

D - Dermatologicals

R - Respiratory system

QD - Dermatologicals

QR - Respiratory system

Pharmacodynamics · 1 item

Used to treat the effects of colds and allergies. Tripelennamine is an antihistamine. Histamine, acting on H<sub>1</sub>-receptors, produces pruritis, vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Tripelennamine is a histamine H1 antagonist. It competes with histamine for the normal H<sub>1</sub>-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.

Mechanism of Action · 6 items

Tripelennamine binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.

Antihistamines used in the treatment of allergy act by competing with histamine for H1-receptor sites on effector cells. They thereby prevent, but do not reverse, responses mediated by histamine alone. Antihistamines antagonize, in varying degrees, most of the pharmacological effects of histamine, including urticaria and pruritus. Also, the anticholinergic actions of most antihistamines provide a drying effect on the nasal mucosa. /Antihistamines/

H1 antagonists inhibit most responses of smooth muscle to histamine. Antagonism of the constrictor action of histamine on respiratory smooth muscle is easily shown in vivo and in vitro. /Histamine Antagonists: H1 Antagonists/

H1 antagonists strongly block the action of histamine that results in increased permeability and formation of edema and wheal. /Histamine Antagonists: H1 Antagonists/

Within the vascular tree, the H1 antagonists inhibit both the vasoconstrictor effects of histamine and, to a degree, the more rapid vasodilator effects that are mediated by H1 receptors on endothelial cells. Residual vasodilatation reflects the involvement of H2 receptors on smooth muscle and can be suppressed only by the concurrent administration of an H2 antagonist. Effects of the histamine antagonists on histamine induced changes in systemic blood pressure parallel these vascular effects. /Histamine Antagonists: H1 Antagonists/

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
UNII
3C5ORO99TY
EC Number
202-100-1
Nikkaji
J4.349D

Tripelenamine is an oily liquid with an amine odor. (NTP, 1992)

Solid

Stability/Shelf LifeSLOWLY DARKENS ON EXPOSURE TO LIGHT /HYDROCHLORIDE/
Dissociation ConstantsPKB= 4.93
Collision Cross Section159.96 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
25 °C · 25°C
Boiling point
0.1 · bp0.1 138-142°; bp1.7 185-190°; bp20 193-205°
Density
1.0683 · 1.0683 (rough estimate)
refractive index
25 · nD25 1.5759-1.5765
pka
3.9 · pKa 3.90±0.08(H2O t undefined I = 0.30 (NaCl)) (Uncertain);8.68±0.06(H2O t undefined I = 0.30 (NaCl)) (Uncertain)
Water Solubility
587.3 mg/L · 587.3mg/L(30 ºC)
Stability
Stable. Incompatible with strong oxidizing agents.
FDA 21 CFR
556.741 · 556.741
FDA UNII
3 C5ORO99TY · 3C5ORO99TY
ATC code
4 AA04,R06AC04 · D04AA04,R06AC04
EPA Substance Registry System
Tripelennamine (91-81-6)
Symbol(GHS)
8 · GHS08,GHS09,GHS05,GHS06
Signal word
Danger
Hazard statements
411 · H411-H373-H331-H302-H318-H361
Precautionary statements
280 · P280-P305+P351+P338-P310-P260-P314-P501-P201-P202-P281-P308+P313-P405-P501-P264-P270-P301+P312-P330-P501-P261-P271-P304+P340-P311-P321-P403+P233-P405-P501
Hazardous Substances Data
91 · 91-81-6(Hazardous Substances Data)
Toxicity
50 oral · LD50 oral in mouse: 152mg/kg
Reactive GroupAmines, Phosphines, and Pyridines
Reactivity Profile · 1 item

TRIPELENAMINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Air and Water ReactionsWater soluble.
Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicology

Interactions · 5 items

Concurrent use /of ototoxic medications/ with antihistamines may mask the symptoms of ototoxicity such as tinnitus, dizziness, or vertigo. /Antihistamines/

Concurrent use of monoamine oxidase (MAO) inhibitors with antihistamines may prolong and intensify the anticholinergic and CNS depressant effects of antihistamines; concurrent use is not recommended. /Antihistamines/

Concurrent use /with alcohol or other CNS depression-producing medications/ may potentiate the CNS depressant effects of either these medications or antihistamines; also, concurrent use of maprotiline or tricyclic antidepressants may potentiate the anticholinergic effects of either antihistamines or these medications. /Antihistamines/

Anticholinergic effects may be potentiated when /anticholinergics or other medications with anticholinergic activity/ are used concurrently with antihistamines; patients should be advised to report occurrence of gastrointestinal problems promptly since paralytic ileus may occur with concurrent therapy. /Antihistamines/

For more Interactions (Complete) data for TRIPELENNAMINE (6 total), please visit the HSDB record page.

Ongoing Test Status · 1 item

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. /Tripelennamine hydrochloride/ [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=154-69-8]

Human Toxicity Excerpts · 5 items

IN CASES OF SYSTEMIC POISONING FROM OVERDOSAGE, OCULAR EFFECTS HAVE BEEN RARE, BUT ISOLATED INSTANCES OF NYSTAGMUS & STRABISMUS HAVE BEEN NOTED, & PUPILS MAY BE DILATED & POORLY RESPONSIVE TO LIGHT.

UNUSUAL CASE OF POISONING BY PYRIBENZAMINE FOLLOWED PERCUTANEOUS APPLICATION OF 2.14 G OF DRUG AS AEROSOL SPRAY ON 8-YR-OLD BOY WITH SEVERE POISON IVY OF TRUNK & EXTREMITIES.

...RIGIDITY, STUPOR, & CIRCULATORY COLLAPSE ARE DESCRIBED IN HUMAN POISONINGS. /HYDROCHLORIDE/

...GI IRRITATION IS COMMON, BUT NOT SEVERE; SEDATION IS MODERATE, & CNS STIMULATION OCCURS OCCASIONALLY. /HYDROCHLORIDE/

For more Human Toxicity Excerpts (Complete) data for TRIPELENNAMINE (13 total), please visit the HSDB record page.

Drug Induced Liver Injury · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

tripelennamine

DILI Positive

Topical, Oral, vaginal

DOI:10.1016/j.drudis.2019.09.022

Antidote and Emergency Treatment · 1 item

THERE IS NO SPECIFIC THERAPY FOR ANTIHISTAMINE POISONING, AND TREATMENT IS ALONG GENERAL SYMPTOMATIC AND SUPPORTIVE LINES. ... SHOULD BREATHING FAIL, MECH SUPPORT OF VENTILATION OFFER SAFER AND ... EFFECTIVE MEANS OF MAINTAINING RESP THAN USE OF ANALEPTICS WHICH ARE PRONE TO INITIATE OR INTENSIFY CONVULSIVE PHASE. /ANTIHISTAMINES/

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Regulatory information

FDA Requirements · 1 item

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Safety data

Toxicity
LD50 oral in mouse: 152mg/kg
Signal word
Danger
Symbol(GHS)
GHS08,GHS09,GHS05,GHS06
Hazard statements
H411-H373-H331-H302-H318-H361
Precautionary statements
P280-P305+P351+P338-P310-P260-P314-P501-P201-P202-P281-P308+P313-P405-P501-P264-P270-P301+P312-P330-P501-P261-P271-P304+P340-P311-P321-P403+P233-P405-P501
Hazardous Substances Data
91-81-6(Hazardous Substances Data)

Many of the H1 antagonists tend to inhibit responses to acetylcholine that are mediated by muscarinic receptors. These atropine like actions are sufficiently prominent in some of the drugs to be manifest during clinical usage ... . /Histamine Antagonists: H1 Antagonists/

Metabolism/Metabolites · 5 items

Hepatic

FROM URINE OF HUMAN ORALLY ADMIN TRIPELENNAMINE, MINOR METAB IDENTIFIED AS N-OXIDE, MAJOR CONJUGATE WAS A UNIQUE QUATERNARY AMMONIUM N-GLUCURONIDE, 2 OTHERS WERE O-GLUCURONIDE OF HYDROXYLATED DERIV. GLUCURONIDE OF HYDROXYTRIPELENNAMINE BEING PRINCIPAL METAB.

MAIN SITE OF METABOLIC TRANSFORMATION IS LIVER. /ANTIHISTAMINES/

H1 blockers are among the many drugs that induce hepatic microsomal enzymes, and they may facilitate their own metabolism. /Histamine Antagonists: H1 Antagonists/

Tripelennamine has known human metabolites that include Tripelennamine N-glucuronide.

MeSH Pharmacological Classification · 2 items

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)

Absorption, Distribution and Excretion · 3 items

Well absorbed in the digestive tract.

The H1 antagonists are well absorbed from the gi tract. Following oral administration, peak plasma concn are achieved in 2 to 3 hr and effects usually last 4 to 6 hr; however, some of the drugs are much longer acting ... . /Histamine Antagonists: H1 Antagonists/

... H1 antagonists are eliminated more rapidly by children than by adults and more slowly in those with severe liver disease. /Histamine Antagonists: H1 Antagonists/

Cellular LocationsMembrane
Metabolite PathwaysTripelennamine H1-Antihistamine Action

Uses & manufacturing

Uses · 4 items

SUNBURN TREATMENT

MEDICATION

MEDICATION (VET)

Use (kg; approx.) in Germany (2009): >25

U.S. Imports · 2 items

(1977) 4.50X10+5 G-PRINCPL CUSTMS DISTS-AS HYDROCHLORIDE

(1979) 9.50X10+5 G-PRINCPL CUSTMS DISTS-AS HYDROCHLORIDE

U.S. Production · 2 items

(1977) GREATER THAN 1.36X10+6 G-INCL SALTS

(1979) GREATER THAN 9.08X10+5 G-INCL CITRATE

Consumption PatternsESSENTIALLY 100% AS AN ANTIHISTAMINIC AGENT (AS CITRATE & HYDROCHLORIDE)
Methods of Manufacturing · 5 items

REACTION OF O-AMINOPYRIDINE AND BETA-DIMETHYLAMINOETHYL CHLORIDE IN THE PRESENCE OF SODAMIDE FOLLOWED BY CONDENSATION WITH BENZYL BROMIDE

...BY SODAMIDE CONDENSATION OF N,N-DIMETHYLAMINOETHYL-2-AMINOPYRIDINE WITH DIMETHYLAMINOETHYL CHLORIDE.

TRIPELENNAMINE IS REACTED WITH EQUIMOLAR PORTION OF CITRIC ACID IN SUITABLE SOLVENT WHICH MAY THEN BE REMOVED BY EVAPORATION. /CITRATE/

TRIPELENNAMINE MAY BE PREPARED AS FOLLOWS: O-AMINOPYRIDINE, PREPARED BY ACTION OF SODAMIDE ON PYRIDINE, IS REACTED WITH BETA-DIMETHYLAMINOETHYL CHLORIDE IN PRESENCE OF SODAMIDE, & RESULTING 2-[2-(DIMETHYLAMINO)ETHYLAMINO]PYRIDINE IS CONDENSED WITH BENZYLBROMIDE IN PRESENCE OF SODAMIDE. /HYDROCHLORIDE/

HYDROCHLORIDE IS FORMED FROM BASE BY TREATMENT WITH HYDROGEN CHLORIDE IN ORG SOLVENT. /HYDROCHLORIDE/

Formulations/Preparations · 2 items

ELIXIR 37.5 MG (EQUIV TO 25 MG OF HYDROCHLORIDE SALT)/5 ML. /CITRATE/

GENERIC: TABLETS, POWDER, CREAM; PBZ-SR (GEIGY) TABLETS (TIMED-RELEASE) 100 MG; PYRIBENZAMINE HYDROCHLORIDE (CIBA): TABLETS 25 & 50 MG, TABLETS (TIMED-RELEASE) 50 MG, CREAM 2% IN 1 OZ CONTAINERS, OINTMENT 2% IN 1 OZ CONTAINERS. /HYDROCHLORIDE/

Use ClassificationPharmaceuticals
Applications · 2 items

UsesMedicine (antihistamine, sunburn treatment).

UsesThis drug lessens the allergic response of the organism caused by histamine. Tripelennamine is used for allergic symptoms, rhinitis, conjunctivitis, and for allergic and anaphylactic reactions. Synonyms of this drug are pelanin and pyribenzamine.

Upstream & downstream products

Upstream raw materials

Sodium amideBenzaldehyde

Suppliers12 total

北京华美互利生物化工010-56205725 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
陕西缔都医药化工有限公司+86-29-87569262 +86-15003564040 · [email protected]
陕西缔都医药化工有限公司029-029-81120477 17792793610 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
上海麦克林生化科技股份有限公司50706066 15221275939 · [email protected]
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
华世药业(南京)有限公司025-57672321 13739186949 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
上海安谱实验科技股份有限公司18502138905 · [email protected]
上海甄准生物科技有限公司18019219489 18901678489 · [email protected]
苏州众联汇创生物医药有限公司13222205691 · [email protected]

Additional notes

DefinitionChEBI: Tripelennamine is an aromatic amine.