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(1R,2S)-(-)-ephedrine hydrochloride
(1R,2S)-(-)-Ephedrine hydrochloride is a pharmaceutical chemical intermediate with formula C10H16ClNO, notable for its use in chemical synthesis and moderate water solubility.
General Material Description
(1R,2S)-(-)-Ephedrine hydrochloride, chemically defined as (1R,2S)-2-(methylamino)-1-phenyl-1-propanol hydrochloride (1:1), is an organic salt with molecular formula C10H16ClNO. It is a solid compound appearing as a crystalline powder, known in chemical and pharmaceutical industries primarily as an intermediate in drug synthesis. The compound exhibits a mild alkaloid characteristic due to the phenylpropanolamine structure and is associated with sensory descriptors related to its pharmacological class rather than flavour or odour. This hydrochloride salt form enhances water solubility compared to the free base and is often handled as the hydrochloride hydrate in laboratory and production settings. It is registered and identified in chemical databases such as PubChem. The compound is typically sourced through synthetic organic chemical processes involving chiral resolution to obtain the (1R,2S) stereoisomer.
Occurrence, Applicability & Potential Uses
While ephedrine naturally occurs in certain species of the Ephedra genus, the (1R,2S)-(-)-ephedrine hydrochloride is predominantly obtained via chemical synthesis for pharmaceutical purposes. This stereoisomer is a precursor and active intermediate in the production of medications related to bronchodilators and decongestants. Regulatory standards such as FEMA (US) and REACH (EU) oversee its use primarily within pharmaceutical manufacturing, not for fragrance or flavour applications. Its modest logP value and water solubility make it amenable for formulation in aqueous-based pharmaceutical solutions. The compound's pharmacological activity is associated with adrenergic receptor interaction, but here the focus is on its chemical role as a defined chirality salt in drug development activities rather than direct consumer use.
Physico-Chemical Properties Summary
(1R,2S)-(-)-Ephedrine hydrochloride presents with a molecular weight of approximately 201.7 g/mol and a chemical formula of C10H16ClNO. It exhibits moderate hydrophilicity evidenced by high water solubility values experimentally measured at 250,000 mg/L at 25 °C, indicating strong aqueous miscibility. The compound has a low vapor pressure of 0.00865 mmHg at 25 °C, which suggests minimal volatility under ambient conditions. Its estimated logP value near 1.05 reflects balanced lipophilic and hydrophilic character, facilitating solubility and bioavailability in aqueous pharmaceutical formulations. The reported flash point, measured at 186 °F (approximately 86 °C), indicates moderate thermal stability. These properties influence the compound's handling, storage, and suitability as a pharmaceutical intermediate rather than as a flavour or fragrance ingredient.
FAQ
What is (1R,2S)-(-)-ephedrine hydrochloride and what are its common names?
(1R,2S)-(-)-Ephedrine hydrochloride is the hydrochloride salt form of a chiral aminopropanol compound widely used as a pharmaceutical intermediate. It is also known by names such as (-)-Ephedrine hydrochloride, L-erythro-ephedrine hydrochloride, and synonyms like (1R,2S)-2-(methylamino)-1-phenyl-1-propanol hydrochloride. Several trade names including Primatene Tablets and Bronkotabs relate to products containing ephedrine derivatives. The compound's molecular formula is C10H16ClNO, and it appears as a crystalline solid.
How is (1R,2S)-(-)-ephedrine hydrochloride used and where does it originate?
This stereoisomer of ephedrine hydrochloride occurs naturally in plants of the Ephedra genus but is predominantly acquired through chemical synthesis for controlled pharmaceutical applications. It serves mainly as a key intermediate in drug manufacturing, especially for respiratory medicines. Regulatory standards, such as REACH (EU), restrict its use to pharmaceutical and chemical synthesis contexts. It is not approved for use as a fragrance or flavour additive due to safety and functional considerations.
What regulations apply to the usage and safety of (1R,2S)-(-)-ephedrine hydrochloride?
(1R,2S)-(-)-Ephedrine hydrochloride is regulated under chemical safety frameworks including REACH in the European Union and monitored by FDA identifiers such as UNII: NLJ6390P1Z in the United States. It is classified without specific hazards under OSHA 29 CFR 1910 but exhibits varying toxicity profiles depending on the administration route and species, as documented in scientific toxicology literature. Recommended usage is limited to pharmaceuticals and chemical synthesis, with explicit contraindications for flavour or fragrance applications. Safety data sheets and authoritative chemical databases provide detailed hazard and handling guidance.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Other Information
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| CHEMBL: | View |
| KEGG (GenomeNet): | D01386 |
| HMDB (The Human Metabolome Database): | Search |
| Export Tariff Code: | 2939.40.5000 |
| ChemSpider: | View |
| Wikipedia: | View |
General Material Information
| Preferred name | (1R,2S)-(-)-ephedrine hydrochloride |
| Trivial Name | (-)-Ephedrine hydrochloride |
| Short Description | (1R,2S)-2-(methylamino)-1-phenyl-1-propanol hydrochloride (1:1) |
| Formula | C10 H16 Cl N O |
| CAS Number | 50-98-6 |
| Deleted CAS Number | 14992-57-5 |
| ECHA Number | 200-074-6 |
| FDA UNII | NLJ6390P1Z |
| Beilstein Number | 3630391 |
| MDL | MFCD00066127 |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 201.6957244873 |
| Vapor Pressure | 0.00865 mmHg @ 25 °C |
| Flash Point TCC Value | 85.6 °C TCC |
| logP (o/w) | 1.054 est |
| Solubility | |
| water, 2.50E+05 mg/L @ 25 °C (exp) | Yes |
| water, 1e+006 mg/L @ 25 °C (est) | Yes |
Safety Information
Safety information
| Preferred SDS: View | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
| intravenous-cat LDLo 60 mg/kg CARDIAC: OTHER CHANGES Medecine Vol. 9, Pg. 59, 1930. intravenous-dog LDLo 70 mg/kg LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Medecine Vol. 9, Pg. 59, 1930. parenteral-frog LDLo 440 mg/kg Manshu Igaku Zasshi. Manchuria Medical Journal. Vol. 3, Pg. 1, 1925. intravenous-guinea pig LD50 98 mg/kg PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: EXCITEMENT Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 59, Pg. 355, 1963. intraperitoneal-hamster LDLo 350 mg/kg CARDIAC: OTHER CHANGES Medecine Vol. 9, Pg. 59, 1930. intraperitoneal-mouse LD50 242 mg/kg Journal of Pharmacology and Experimental Therapeutics. Vol. 158, Pg. 135, 1967. intravenous-mouse LD50 95 mg/kg Journal of Pharmacology and Experimental Therapeutics. Vol. 95, Pg. 336, 1949. oral-mouse LD50 400 mg/kg Journal of Medicinal Chemistry. Vol. 9, Pg. 966, 1966. parenteral-mouse LDLo 500 mg/kg Manshu Igaku Zasshi. Manchuria Medical Journal. Vol. 3, Pg. 1, 1925. intramuscular-rabbit LD50 175 mg/kg Journal of Pharmacology and Experimental Therapeutics. Vol. 86, Pg. 284, 1946. intravenous-rabbit LD50 65 mg/kg Journal of Pharmacology and Experimental Therapeutics. Vol. 95, Pg. 336, 1949. intraperitoneal-rat LD50 165 mg/kg Journal of Pharmacology and Experimental Therapeutics. Vol. 86, Pg. 284, 1946. intravenous-rat LD50 69 mg/kg Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 33, Pg. 80, 1944. | |
| Dermal Toxicity: | |
| subcutaneous-dog LDLo 220 mg/kg LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Medecine Vol. 9, Pg. 59, 1930. subcutaneous-frog LDLo 400 mg/kg LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE Medecine Vol. 9, Pg. 59, 1930. subcutaneous-guinea pig LD50 192 mg/kg PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: EXCITEMENT Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 59, Pg. 355, 1963. subcutaneous-mouse LD50 40870 ug/kg BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: EXCITEMENT Journal of Pharmacology and Experimental Therapeutics. Vol. 87, Pg. 214, 1946. subcutaneous-rabbit LD50 165 mg/kg Journal of Pharmacology and Experimental Therapeutics. Vol. 86, Pg. 284, 1946. subcutaneous-rat LD50 1150 mg/kg Journal of Pharmacology and Experimental Therapeutics. Vol. 95, Pg. 336, 1949. | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| pharmaceuticals / chemical synthisis | |||
| Recommendation for (1R,2S)-(-)-ephedrine hydrochloride usage levels up to: | |||
| not for fragrance use. | |||
| Recommendation for (1R,2S)-(-)-ephedrine hydrochloride flavor usage levels up to: | |||
| not for flavor use. | |||
Safety references
| EPI System: View |
| ClinicalTrials.gov:search |
| Daily Med:search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):50-98-6 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :65326 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:1 |
| (1R,2S)-2-(methylamino)-1-phenylpropan-1-ol;hydrochloride |
| Chemidplus:0000050986 |
| RTECS:KB1750000 for cas# 50-98-6 |