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Synephrine

Synephrine structure

CAS No:
94-07-5
Formula:
C9H13NO2
Chemical Name:
Synephrine
Synonyms:
Benzenemethanol,4-hydroxy-α-[(methylamino)methyl]-;Benzyl alcohol,p-hydroxy-α-[(methylamino)methyl]-;4-Hydroxy-α-[(methylamino)methyl]benzenemethanol;Analeptin;p-Hydroxy-α-[(methylamino)methyl]benzyl alcohol;1-(4-Hydroxyphenyl)-N-methylethanolamine;β-Methylamino-α-(4-hydroxyphenyl)ethyl alcohol;Oxedrine;Parasympatol;Simpalon;Sympathol;Synephrin;Synephrine;Synthenate;Simpatol;S 38537-9;Sympaethamine;Sympaethamin;1-(4-Hydroxyphenyl)-2-(methylamino)ethanol;dl-1-(4-Hydroxyphenyl)-2-(methylamino)ethanol;(±)-Synephrine;(±)-N-Methyloctopamine;(±)-S38537-9;DL-Synephrine;1-Hydroxy-4-[(1-hydroxy-2-methylamino)ethyl]benzene;Ethaphene;NSC 166285;NSC 170956;N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]-N-methylamine;Advantra Z;582-84-3;860222-98-6
Categories:
Cosmetic Ingredient > Skin Protecting

Description

Synephrine (Oxedrine) is an α-adrenergic and β-adrenergic agonist derived from the Citrus aurantium, it has sympathomimetic and structural similarities to ephedra and ephedrine alkaloids[1][2].

Solid

Synephrine is a phenethylamine alkaloid that is 4-(2-aminoethyl)phenol substituted by a hydroxy group at position 1 and a methyl group at the amino nitrogen. It has a role as a plant metabolite and an alpha-adrenergic agonist. It is a phenethylamine alkaloid, a member of phenols and a member of ethanolamines. It is a conjugate base of a synephrinium.|Synephrine, also referred to as, p-synephrine, is naturally occurring alkaloid. It is present in approved drug products as neo-synephrine, its m-substituted analog. p-synephrine and m-synephrine are known for their longer acting adrenergic effects compared to norepinephrine. The similarity of naming between m-synephrine and the unsubstituted form, synephrine, is a source of some confusion however m-synephrine refers to a related drug more commonly known as phenylephrine. While the compounds share some chemical and pharmacological similarities, they are in fact distinct chemical entities.|Sympathetic alpha-adrenergic agonist with actions like PHENYLEPHRINE. It is used as a vasoconstrictor in circulatory failure, asthma, nasal congestion, and glaucoma.

Synephrine Basic Attributes

Molecular Weight：

167.205

Exact Mass：

167.21

EC Number：

202-300-9

NSC Number：

759316|170956|166285

DSSTox ID：

DTXSID0030588

ATC Code：

C - Cardiovascular system|S - Sensory organs

HScode：

2922509090

Characteristics

PSA：

52.49000

XLogP3：

-0.03

Appearance：

Solid

Density：

1.2±0.1 g/cm3

Melting Point：

184.5 °C

Boiling Point：

341.1±27.0 °C at 760 mmHg

Flash Point：

163.4±14.3 °C

Refractive Index：

1.572

Water Solubility：

0.0004265 mg/L @ 25 °C (est)

Storage Conditions：

2-8ºC

Collision Cross Section：

134.4 Å² [M+H-H2O]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|132 Å² [M+H-H2O]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R36/37/38

safety instructions：

S26-S36

RTECS Number：

DO7350000

Marks：

Xi:Irritant;

Stability/Shelf Life：

Stable at normal temperatures and pressures.

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (97.67%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 43 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

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) (See all compounds classified as Nasal Decongestants.)|Drugs that selectively bind to and activate alpha adrenergic receptors. (See all compounds classified as Adrenergic alpha-Agonists.)|Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. (See all compounds classified as Sympathomimetics.)|Drugs used to cause constriction of the blood vessels. (See all compounds classified as Vasoconstrictor Agents.)

MeSH Entry Terms：

Oxedrine

Synephrine Use and Manufacturing

A α-adrenergic receptor agonist, vasoconstrictor. anti-obesity A a-adrenergic receptor agonist, vasoconstrictor

Computed Properties

Molecular Weight:167.20
XLogP3:-0.6
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:167.094628657
Monoisotopic Mass:167.094628657
Topological Polar Surface Area:52.5
Heavy Atom Count:12
Complexity:122
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Guide of Synephrine

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
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