4-Benzyloxyphenyl-n-butylcarbamate (URB532) CAS No. 195140-79-5

Product Description

4-Benzyloxyphenyl-n-butylcarbamate—also catalogued as URB532 or FAAH Inhibitor I—is a synthetic carbamate. Structurally, it couples a para-benzyloxyphenyl moiety (a phenyl ring bearing a –OCH₂C₆H₅ substituent at the 4-position) to an n-butylcarbamate fragment (–NHCOOC₄H₉) in which the carbamate nitrogen is attached to the phenyl ring and the ester oxygen bears the straight-chain n-butyl group. The compound is readily prepared from 4-hydroxyphenyl carbamate (or 4-aminophenol) by sequential carbamate formation with n-butyl chloroformate and Williamson etherification with benzyl bromide. Its primary significance lies in its potent, reversible inhibition of fatty acid amide hydrolase (FAAH), the enzyme responsible for degrading endocannabinoids such as anandamide; by elevating endocannabinoid tone, URB532 has been employed as a pharmacological probe in neuro- and metabolic-disease research and explored as a lead structure for carbamate-based therapeutics.

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Product Use & Characteristics

Basic Identity

• Molecular Formula: C₁₈H₂₁NO₃

• Molecular Weight: 299.4 g/mol

• IUPAC Name: (4-phenylmethoxyphenyl) N-butylcarbamate

• Synonyms: URB532, FAAH Inhibitor I, 4-(Benzyloxy)phenyl butylcarbamate, n-butylcarbamic acid 4-benzyloxyphenyl ester

Structure & Chemistry

• Core Scaffold: Carbamate (R¹–NH–COO–R²)

  • R¹ (N-substituent): 4-(benzyloxy)phenyl

  • R² (O-substituent): n-butyl

• Functional Groups:

  • Para-benzyloxy substituent (–OCH₂C₆H₅) on phenyl ring

  • Carbamate linkage (–NHCOO–) providing reversible FAAH inhibition

Mechanism of Action

• Primary Target: Fatty acid amide hydrolase (FAAH)

• Mechanism: Reversible inhibition → blocks degradation of endocannabinoids

  • Elevates anandamide (AEA), palmitoylethanolamide (PEA) & related fatty-acid amides

  • Enhances CB1/CB2 receptor signaling indirectly

Why us!

Qingdao Sigma Chemical Co., Ltd., established in January 2017 and headquartered in Qingdao, China, is a reliable chemical supplier. Specializing in pharmaceuticals, biochemical intermediates, and research chemicals, the company offers a diverse product portfolio, including peptides (e.g., Tirzepatide, Semaglutide), nootropics, veterinary products, and APIs, often marketed with ≥99% purity and COA certification. We provides R&D, custom synthesis, and contract manufacturing services at various scales, while claiming a global export presence across 100+ countries. With international warehouses in the USA, Europe, Australia, and Canada, Qingdao Sigma Chemical also facilitates drop-shipping and reshipments, positioning itself as a key supplier for laboratory and research applications.