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2-[(1R)-3-(dipropan-2-ylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenol(CAS#207679-81-0) Featured Image
  • 2-[(1R)-3-(dipropan-2-ylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenol(CAS#207679-81-0) 1

2-[(1R)-3-(dipropan-2-ylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenol(CAS#207679-81-0)

Chemical Property:

Molecular Formula C22H31NO2
Molar Mass 341.49
Density 1.060±0.06 g/cm3(Predicted)
Melting Point 68-72°C
Boling Point 490.7±45.0 °C(Predicted)
Flash Point 233.165°C
Solubility DMSO (Slightly), Methanol (Slightly)
Vapor Presure 0mmHg at 25°C
Appearance Solid
Color Off-White to Pale Yellow
pKa 9.61±0.48(Predicted)
Storage Condition -20°C Freezer
Refractive Index 1.563
In vitro study 5-hydroxymethyl tolterodine is a major pharmacologically active metabolite of tolterodine. 5-hydroxymethyl tolterodine competitively inhibits carbacol-induced contraction of isolated guinea pig bladder strips with concentration-dependent characteristics. 5-hydroxymethyl tolterodine antagonized the muscarinic receptor with a pA 2 value of 9.1. 5-hydroxymethyl tolterodine can inhibit (-) 5-hydroxymethyl tolterodine in guinea pig bladder, parotid gland, heart and cerebral cortex homogenates with pharmacological properties similar to that of tolterodine. Intravenous injection of 5-hydroxymethyl tolterodine inhibits bladder volume-induced bladder contraction, which is representative of micturition pressure, in a dose-dependent manner.
In vivo study 5-hydroxymethyl tolterodine inhibited acetylcholine-induced bladder contraction in anesthetized cats more effectively than electrical stimulation-induced salivation with ID50 of 15 and 40 nmol/kg, respectively. 5-hydroxymethyl tolterodine is three times more effective in the bladder than in the salivary glands.

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2-[(1R)-3-(dipropan-2-ylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenol(CAS#207679-81-0)

Physicochemical properties
It is generally white or off-white crystalline powder, which has a certain solubility in organic solvents such as methanol, ethanol, methylene chloride, etc., and is slightly soluble in water.
Structural features
The molecule contains a benzene ring with a chiral (R)-3-(diisopropylamino)-1-phenylpropyl side chain attached to the 2 positions and a hydroxymethyl group attached to the 4 positions. Among them, the diisopropyl amino group has a certain alkalinity, and the benzene ring and hydroxymethyl groups make the molecule have a certain hydrophilicity and chemical reactivity.
Fields of application
Pharmaceutical intermediates: It is an important intermediate in the synthesis of some drugs for the treatment of urological diseases, such as in the process of synthesizing tolterodine tartrate and other drugs, (R)-5-hydroxymethyl tolterodine is one of the key intermediates, which participates in the construction of the molecular structure of the drug and plays an important role in the activity and selectivity of the drug.
Drug impurity reference substance: It can be used as an impurity reference for drugs such as fesolodine, which is used in drug quality control and analysis and testing, and determines the presence and content of impurities in the drug by comparing it with drug samples to ensure the quality and safety of the drug.

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