Pseudococaine | CAS:478-73-9 | Manufacturer ChemFaces

Pseudococaine

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Description:

Pseudococaine produces high-voltage slow waves (HVSWs) in the EEG associated with behavioral depression, it is more potent than cocaine in producing convulsions in the same monkeys.

In vivo:

Brain Res Bull. 1978 Jul-Aug;3(4):341-7.

Cocaine and pseudococaine: comparative effects on electrical after-discharge in the limbic system of cats.[Pubmed: 318203 ]

METHODS AND RESULTS:
The effects of cocaine and its dextroisomer Pseudococaine on electrical after-discharge (AD) evoked by electrical stimulation of the hippocampus or amygdala were studied in cats with electrodes implanted in the brain. Intravenous injection of cocaine (2.0 to 4.0 mg/kg doses) produced a suppressive effect on the AD while producing low-voltage fast waves (LVFWs) in the electrical activities of the brain (EEG) associated with behavioral excitation. In contrast, Pseudococaine at the same dose as cocaine failed to show a significant suppressive effect on the AD except at high doses (5.0 mg/kg). Pseudococaine produced high-voltage slow waves (HVSWs) in the EEG associated with behavioral depression. A linear dose-response relationship was observed for the suppressive effect of cocaine on the AD.
CONCLUSIONS:
The results suggested that the limbic system may be involved as a primary site of action of cocaine in the central nervous system (CNS).

Brain Res Bull. 1977 Nov-Dec;2(6):417-24.

Comparison of the convulsant effects of cocaine and pseudococaine in the rhesus monkey.[Pubmed: 414826]

METHODS AND RESULTS:
The convulsant effects of cocaine and its C2-epimer, Pseudococaine on EEG, respiration, heart rate and behavior were studied in the rhesus monkeys with electrodes implanted in the brain. Intravenous injections of cocaine (3.0 to 8.0 mg/kg) and Pseudococaine (3.0 to 7.0 mg/kg) in the animals produced a similar pattern of clonic convulsions accompanied by marked increases in the heart and respiratory rates with mydriasis and excessive salivation. However, both isomers showed different effects on the EEG and animal's behavior following convulsions; e.g., the cocaine-induced convulsions were followed by low-voltage fast waves in the EEGs associated with behavioral hyperexcitation, while Pseudococaine-induced convulsions were followed by high-voltage slow waves associated with behavioral depression and drowsiness with intermittent sleep.
CONCLUSIONS:
Pseudococaine was more potent than cocaine in producing convulsions in the same monkeys. The durations of convulsions produced by these drugs were dose-dependent.

Pseudococaine Description

Source:	The leaves of the coca plant .
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Animal Research:

Psychopharmacology (Berl). 1978 Apr 14;57(1):13-20.

Comparative effects of cocaine and pseudococaine on EEG activities, cardiorespiratory functions, and self-administration behavior in the rhesus monkey.[Pubmed: 96463]

The effects of cocaine and Pseudococaine on the EEGs, heart and respiratory rates, and self-administration behavior were studied in rhesus monkeys.
METHODS AND RESULTS:
An intravenous injection of cocaine (2.5 and 4.0 mg/kg) in the monkey produced low-voltage fast waves (LVFWs) in the EEGs and behavioral hyperexcitation accompanied by marked increases in the heart and respiratory rates with mydriasis and excessive salivation. In contrast, Pseudococaine produced high-voltage slow waves (HVSWs) in the EEGs and behavioral depression accompanied by the same symptoms of the autonomic functions as those produced by cocaine. Both isomers were self-administered by the monkeys. During cocaine self-administration sessions, the animals showed hyperexcitation in their overall behavior, while with Pseudococaine they showed almost normal behavioral responses.
CONCLUSIONS:
These results suggest that cocaine produced excitatory effects and Pseudococaine inhibitory effects on the EEGs and behavior. Both isomers stimulate the heart and respiratory rates, and were self-administered by the monkeys.

Structure Identification:

Org Lett. 2012 Aug 17;14(16):4278-81.

Asymmetric synthesis of the tropane alkaloid (+)-pseudococaine via ring-closing iodoamination.[Pubmed: 22866940]

METHODS AND RESULTS:
Ring-closing iodoamination of tert-butyl 2-hydroxy-7-[N-methyl-N-(α-methyl-p-methoxybenzyl)amino]cyclohept-3-ene-1-carboxylates proceeds with concomitant loss of the N-α-methyl-p-methoxybenzyl group to give the corresponding 8-azabicyclo[3.2.1]octane scaffolds in >99:1 dr. Subsequent elaboration of one of these templates provided access to (+)-Pseudococaine hydrochloride, in seven steps and 31% overall yield from commercially available starting materials.

J Forensic Sci. 1994 Nov;39(6):1537-43.

Detection and determination of pseudococaine in coca leaves and illicit cocaine samples.[Pubmed: 7815033]

METHODS AND RESULTS:
Methodology is presented for the isolation, identification and determination of Pseudococaine in coca leaves and illicit cocaine. Coca leaves, crude cocaine base (coca paste), refined cocaine base and refined cocaine hydrochloride, all derived from the same geographic location in Bolivia, were examined. Pseudococaine and other coca alkaloids were isolated from leaf samples using toluene extraction followed by acid/Celite trap and ion-pair column chromatography, and from crude and refined cocaine samples by acid/Celite column ion-pairing chromatography.
CONCLUSIONS:
Mass spectral analysis of coca leaf isolates confirmed the presence of Pseudococaine. Pseudococaine was quantified by capillary gas chromatography with flame ionization detection at levels of 0.0001-0.035% (relative to cocaine) in refined illicit cocaine and coca leaves.

Product Name	Pseudococaine
Price:
CAS No.:	478-73-9
Catalog No.:	CFN00184
Molecular Formula:	C₁₇H₂₁NO₄
Molecular Weight:	303.35 g/mol
Purity:	>=98%
Type of Compound:	Alkaloids
Physical Desc.:	Cryst.
Source:	The leaves of the coca plant .
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Inhibitors Compound Library Alkaloids Compound Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	3.2965 mL	16.4826 mL	32.9652 mL	65.9304 mL	82.4131 mL
5 mM	0.6593 mL	3.2965 mL	6.593 mL	13.1861 mL	16.4826 mL
10 mM	0.3297 mL	1.6483 mL	3.2965 mL	6.593 mL	8.2413 mL
50 mM	0.0659 mL	0.3297 mL	0.6593 mL	1.3186 mL	1.6483 mL
100 mM	0.033 mL	0.1648 mL	0.3297 mL	0.6593 mL	0.8241 mL

CFN00148	Anisodine	52646-92-1	319.36	C₁₇H₂₁NO₅
CFN00149	Apoatropine	500-55-0	271.36	C₁₇H₂₁NO₂
CFN00150	Apohyoscine	535-26-2	285.34	C₁₇H₁₉NO₃
CFN00151	Aponorhyoscine	25650-56-0	271.31	C₁₆H₁₇NO₃
CFN00171	Nortropacocaine	18470-33-2	231.29	C₁₄H₁₇NO₂
CFN00177	Bellendine	32152-73-1	205.26	C₁₂H₁₅NO₂
CFN00181	Brugine	14912-30-2	273.42	C₁₂H₁₉NO₂S₂
CFN00182	Chalcostrobamine	75638-72-1	269.34	C₁₇H₁₉NO₂
CFN00183	Cocaine	50-36-2	303.35	C₁₇H₂₁NO₄
CFN00184	Pseudococaine	478-73-9	303.35	C₁₇H₂₁NO₄