[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate

C17H23NO3

CAS51-55-8
GHS06 Gefahrensymbol: Giftig – Totenkopf mit Knochen
Danger

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Identification

CAS Number
51-55-8
EC Number
200-104-8
UN Number
1544
Index Number
614-010-00-3
PubChem CID
174174

Physical-chemical properties

Molecular Formula
C17H23NO3
Molar Mass
289.40 g/mol
IUPAC Name
[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate

Chemical Identifiers

InChI
InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15?,16?
InChI Key
RKUNBYITZUJHSG-PJPHBNEVSA-N

Overview

[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate (CAS 51-55-8) is a tropane alkaloid ester with potent local anesthetic and stimulant properties. This bicyclic compound, with molecular formula C17H23NO3 and molar mass 289.4 g/mol, represents a significant pharmaceutical intermediate in the tropane alkaloid family. The substance features a characteristic 8-azabicyclo[3.2.1]octane core structure, which is fundamental to its biological activity and distinguishes it from other nitrogen-containing heterocycles such as N-methylaniline derivatives. Its stereochemical configuration at positions 1S and 5R is crucial for its pharmacological properties. The compound exhibits high acute toxicity (Acute Tox. 2), requiring careful handling protocols and specialized safety measures. It falls under ADR transport class 6.1 and carries the GHS06 pictogram with a "Danger" signal word, indicating its potential health hazards. Storage and handling must comply with strict regulatory requirements due to its toxicological profile. Industrial applications include use as a research chemical in pharmaceutical development, particularly in studies involving sodium channel blockers and local anesthetics. It serves as a reference standard in analytical chemistry laboratories and quality control processes. The compound is also utilized in biochemical research for investigating neurological pathways and receptor binding studies, where its structural similarity to other complex heterocycles like (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one makes it valuable for comparative studies. OYSI maintains reliable supply chains for this specialized pharmaceutical intermediate, ensuring consistent availability for qualified research institutions and pharmaceutical manufacturers across Europe.

Safety & Classification

Danger
Classification:

Acute Tox. 2 *; Acute Tox. 2 *

HHazard Statements (H-Statements)

Describe the nature and severity of the hazard

H330

Fatal if inhaled.

H300

Fatal if swallowed.

Classification according to CLP Regulation (EC) No 1272/2008. The complete list of hazard and precautionary statements can be found in the Safety Data Sheet (SDS).

First Aid Measures

Inhalation

Fatal

Measures if vapours or dust are inhaled

First Aid Actions

  • +P304IF INHALED:
  • +P340Remove person to fresh air and keep comfortable for breathing.
  • +P311Call a POISON CENTER/doctor.

Related hazard statements:

Ingestion

Fatal

Measures if substance is accidentally swallowed

First Aid Actions

  • +P301IF SWALLOWED:
  • +P330Rinse mouth.
  • +P331Do NOT induce vomiting.
  • +P310Immediately call a POISON CENTER/doctor.

Related hazard statements:

General Measures

Emergency 112 | Poison Control: +49 30 19240 (DE), +33 1 45 42 59 59 (FR), +31 30 274 88 88 (NL)

First aid measures are based on CLP classification and associated P-statements. They do not replace the Safety Data Sheet (SDS). In case of emergency, always consult the full SDS and a physician.

Transport (ADR)

UN Number1544
ADR Class6.1
Packing GroupI
Tunnel CodeC/E
Proper Shipping NameAtropin
Marine PollutantNo

Frequently Asked Questions

What is [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate?

[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate is a tropane alkaloid derivative with the molecular formula C17H23NO3 and CAS number 51-55-8. This compound features a bicyclic tropane structure linked to a phenylpropanoate ester group. With a molecular weight of 289.4 g/mol, it belongs to the class of highly toxic substances, classified as Acute Tox. 2 under GHS regulations, requiring careful handling due to its significant toxicological properties.

What are the physicochemical properties of [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate?

[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate is an organic compound with molecular formula C17H23NO3 and molecular weight 289.4 g/mol. As a tropane alkaloid ester, it typically appears as a crystalline solid at room temperature. The compound contains both hydrophilic (hydroxyl and amine groups) and lipophilic (phenyl and bicyclic) regions, affecting its solubility profile. Its stereochemistry is specifically defined with (1S,5R) configuration at the bicyclic system.

What is [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate used for?

[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate is primarily used in pharmaceutical research and analytical chemistry applications. Due to its tropane alkaloid structure, it serves as a reference standard in analytical laboratories and research institutions. The compound may also be utilized in medicinal chemistry research for studying structure-activity relationships. Given its high toxicity classification (Acute Tox. 2), its use is restricted to specialized professional applications under controlled laboratory conditions.

How to handle [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate safely?

[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate requires extreme caution due to its Acute Tox. 2 classification and GHS06 pictogram. Essential PPE includes chemical-resistant gloves, safety goggles, and laboratory coats. Work must be conducted in well-ventilated areas or under fume hoods. Avoid skin contact, inhalation, and ingestion. Use only the minimum quantities necessary and ensure proper training before handling. Emergency equipment should be readily available, and work should be performed by qualified personnel only.

How to store [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate correctly?

[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate must be stored in a secure, locked chemical storage area due to its high toxicity (Acute Tox. 2). Keep containers tightly closed in a cool, dry, well-ventilated location away from heat and ignition sources. Store separately from incompatible materials including strong oxidizers and acids. Access should be restricted to authorized personnel only. Regular inventory checks and proper labeling with GHS06 hazard symbols are essential for safe storage management.

What to do in case of contact with [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate?

Immediate medical attention is required for any contact with [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate due to its Acute Tox. 2 classification. For skin contact, remove contaminated clothing and rinse thoroughly with water for at least 15 minutes. If inhaled, move to fresh air immediately. In case of eye contact, flush with water for 15 minutes. If ingested, do not induce vomiting and seek immediate medical care. Always contact poison control or emergency services promptly.

How to dispose of [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate properly?

[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate must be disposed of as hazardous waste due to its high toxicity classification. Contact licensed hazardous waste disposal companies for proper handling and destruction. Never dispose of in regular waste, drains, or sewage systems. Small laboratory quantities should be collected in appropriate hazardous waste containers and labeled clearly. Follow local and national regulations for hazardous waste disposal, and maintain disposal records as required by environmental authorities.

How to transport [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate?

[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate is classified as ADR Class 6.1, Packing Group I, indicating high toxicity for transport purposes. Shipments require proper dangerous goods packaging, labeling with toxic substance markings, and appropriate shipping documentation. Only certified dangerous goods carriers can transport this material. Packaging must meet UN specification requirements for Packing Group I substances. Emergency response information and safety data sheets must accompany all shipments to ensure safe handling during transport.

Is [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate subject to specific regulations?

[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate is subject to extensive regulatory oversight due to its high toxicity. Under CLP regulation, it carries Acute Tox. 2 classification with mandatory GHS06 labeling. REACH registration may be required for commercial use in the EU. The compound is not currently listed as SVHC, but its toxicity profile means it may be subject to additional restrictions. Transport regulations under ADR Class 6.1 apply, and local controlled substance regulations should be verified before purchase or use.

Where to buy [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate in Europe?

[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate is available through OYSI, a specialized European distributor of high-quality chemical products. As a highly toxic substance (Acute Tox. 2), procurement requires proper authorization and compliance verification. OYSI ensures full regulatory compliance, proper packaging, and safe delivery throughout Europe. Due to the compound's toxicity classification and transport restrictions (ADR 6.1, Group I), purchases are limited to qualified research institutions and licensed facilities with appropriate handling capabilities.

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[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate is a dangerous good. We support you with labeling, packaging, and transport documentation.

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Data Sources

Classification per CLP Regulation (EC) No 1272/2008. Data from ECHA and PubChem.