AM404

Modify Date: 2024-01-08 12:16:17

AM404 Structure
AM404 structure
Common Name AM404
CAS Number 183718-77-6 Molecular Weight 395.578
Density 1.0±0.1 g/cm3 Boiling Point 579.4±50.0 °C at 760 mmHg
Molecular Formula C26H37NO2 Melting Point N/A
MSDS USA Flash Point 304.2±30.1 °C
Symbol GHS02 GHS07
GHS02, GHS07
Signal Word Danger

 Use of AM404


AM404, an inhibitor of endocannabinoid reuptake, blocks anandamide transport with IC50 values in the low micromolar range[1]. AM404 is able to relax rat isolated hepatic arteries contracted with Phenylephrine, with a pEC50 value of 7.4 (corresponding to an EC50 of 0.04 µM). Neuroprotective Effect[2].

 Names

Name N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide
Synonym More Synonyms

 AM404 Biological Activity

Description AM404, an inhibitor of endocannabinoid reuptake, blocks anandamide transport with IC50 values in the low micromolar range[1]. AM404 is able to relax rat isolated hepatic arteries contracted with Phenylephrine, with a pEC50 value of 7.4 (corresponding to an EC50 of 0.04 µM). Neuroprotective Effect[2].
Related Catalog
In Vitro AM404 reduces C6 glioma cell proliferation with IC50 values of 4.9 µM. AM404 non-specifically inhibit C6 glioma cell proliferation at concentrations used to block the cellular accumulation of the endocannabinoid anandamide[2]. Cell Viability Assay[2] Cell Line: Rat C6 glioma cells Concentration: 1, 3, 10 and 30 µM Incubation Time: 24, 48, 72 and 96 h Result: Produced a concentration-dependent reduction in cell proliferation that was seen with 24 h of exposure to 10 and 30 µM concentrations and after 48 h at 3 µM. The lowest concentration of AM404 tested, 1 µM, produced a significant, albeit small, reduction in cell proliferation at 72 h.
In Vivo AM404 (1-5 mg/kg, i.p.) exerts dose-dependent anxiolytic-like effects in the three models: elevated plus maze, defensive withdrawal and separation-induced ultrasonic vocalizations. Animal Model: Adult male Sprague-Dawley rats (250-300 g)[2] Dosage: 2.5-10 mg/kg Administration: Intraperitoneal (i.p.) Result: Caused a dose-dependent increase in anandamide levels in prefrontal cortex, hippocampus and thalamus.
References

[1]. A Giuffrida, et al. Mechanisms of endocannabinoid inactivation: biochemistry and pharmacology. J Pharmacol Exp Ther. 2001 Jul;298(1):7-14.

[2]. Kent-Olov Jonsson, et al. AM404 and VDM 11 non-specifically inhibit C6 glioma cell proliferation at concentrations used to block the cellular accumulation of the endocannabinoid anandamide. Arch Toxicol. 2003 Apr;77(4):201-7.

[3]. Marco Bortolato, et al. Anxiolytic-like properties of the anandamide transport inhibitor AM404. Neuropsychopharmacology. 2006 Dec;31(12):2652-9.

 Chemical & Physical Properties

Density 1.0±0.1 g/cm3
Boiling Point 579.4±50.0 °C at 760 mmHg
Molecular Formula C26H37NO2
Molecular Weight 395.578
Flash Point 304.2±30.1 °C
Exact Mass 395.282440
PSA 49.33000
LogP 7.63
Vapour Pressure 0.0±1.7 mmHg at 25°C
Index of Refraction 1.555

 MSDS


SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name: N-(4-Hydroxyphenyl)-arachidonylamide
REACH No.: A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No.: 183718-77-6
Relevant identified uses of the substance or mixture and uses advised against
Identified uses: Laboratory chemicals, Manufacture of substances



SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Flammable liquids (Category 2), H225
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
F Highly flammableR11
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal wordDanger
Hazard statement(s)
H225Highly flammable liquid and vapour.
Precautionary statement(s)
P210Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
Supplemental Hazardnone
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)F Highly flammable
R-phrase(s)
R11Highly flammable.
S-phrase(s)
S16Keep away from sources of ignition - No smoking.
Caution - this mixture contains a substance not yet fully tested.
Other hazards - none

SECTION 3: Composition/information on ingredients
Mixtures
Synonyms: AM404
Formula: C26H37NO2 C26H37NO2
Molecular Weight: 395,58 g/mol
No components need to be disclosed according to the applicable regulations.
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Do NOT induce vomiting. Never give anything by mouth to an unconscious person. Rinse mouth with
water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
Use water spray to cool unopened containers.

SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation.
Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapours accumulating to
form explosive concentrations. Vapours can accumulate in low areas.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and
place in container for disposal according to local regulations (see section 13).
Reference to other sections
For disposal see section 13.

SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid inhalation of vapour or mist.
Keep away from sources of ignition - No smoking.Take measures to prevent the build up of electrostatic
charge.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Recommended storage temperature: -20 °C
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Face shield and safety glasses Use equipment for eye protection tested and approved under
appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Impervious clothing., Flame retardant antistatic protective clothing, The type of protective
equipment must be selected according to the concentration and amount of the dangerous
substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator
with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup
to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) AppearanceForm: liquid
b) Odourno data available
c) Odour Thresholdno data available
d) pHno data available
e) Melting point/freezingno data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point14 °C - closed cup
h) Evaporation rateno data available
i) Flammability (solid, gas) no data available
j) Upper/lowerno data available
flammability or
explosive limits
k) Vapour pressureno data available
l) Vapour densityno data available
m) Relative densityno data available
n) Water solubilityno data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignitionno data available
temperature
q) Decompositionno data available
temperature
r) Viscosityno data available
s) Explosive propertiesno data available
t) Oxidizing propertiesno data available
Other safety information
no data available

SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
Heat, flames and sparks. Extremes of temperature and direct sunlight.
Incompatible materials
Oxidizing agents, Alkali metals, Ammonia, Peroxides
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC:No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
Central nervous system depression, narcosis, Nausea, Dizziness, Damage to the heart., To the best of our
knowledge, the chemical, physical, and toxicological properties have not been thoroughly investigated.
Heart - Irregularities - Based on Human Evidence

SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

SECTION 13: Disposal considerations
Waste treatment methods
Product
Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting
as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal
company.
Contaminated packaging
Dispose of as unused product.

SECTION 14: Transport information
UN number
ADR/RID: 1170IMDG: 1170IATA: 1170
UN proper shipping name
ADR/RID: ETHANOL
IMDG: ETHANOL
IATA:Ethanol
Transport hazard class(es)
ADR/RID: 3IMDG: 3IATA: 3
Packaging group
ADR/RID: IIIMDG: IIIATA: II
Environmental hazards
ADR/RID: noIMDG Marine Pollutant: noIATA: no
Special precautions for user
no data available



SECTION 15 - REGULATORY INFORMATION
N/A


SECTION 16 - ADDITIONAL INFORMATION
N/A

 Safety Information

Symbol GHS02 GHS07
GHS02, GHS07
Signal Word Danger
Hazard Statements H225-H319
Precautionary Statements P210-P280-P305 + P351 + P338-P337 + P313-P403 + P235
Personal Protective Equipment Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter
Hazard Codes F: Flammable;
Risk Phrases R36/37/38
Safety Phrases S7
RIDADR UN 1170 3/PG 2

 Articles4

More Articles
Cannabidiol enhances anandamide signaling and alleviates psychotic symptoms of schizophrenia.

Transl. Psychiatry 2 , e94, (2012)

Cannabidiol is a component of marijuana that does not activate cannabinoid receptors, but moderately inhibits the degradation of the endocannabinoid anandamide. We previously reported that an elevatio...

The anandamide transport inhibitor AM404 reduces the rewarding effects of nicotine and nicotine-induced dopamine elevations in the nucleus accumbens shell in rats.

Br. J. Pharmacol. 165(8) , 2539-48, (2012)

The fatty acid amide hydrolase inhibitor URB597 can reverse the abuse-related behavioural and neurochemical effects of nicotine in rats. Fatty acid amide hydrolase inhibitors block the degradation (an...

Elevated circulating levels of anandamide after administration of the transport inhibitor, AM404.

Eur. J. Pharmacol. 408(2) , 161-8, (2000)

The biological actions of the endogenous cannabinoid anandamide are terminated by carrier-mediated transport into neurons and astrocytes, followed by enzymatic hydrolysis. Anandamide transport is inhi...

 Synonyms

N-(4-Hydroxyphenyl)-arachidonylamide
5,8,11,14-Eicosatetraenamide, N-(4-hydroxyphenyl)-, (5Z,8Z,11Z,14Z)-
AM 404
(5Z,8Z,11Z,14Z)-N-(4-Hydroxyphenyl)icosa-5,8,11,14-tetraenamide
N-(4-Hydroxyphenyl)arachidonylamide
AM-404
AM404
(5Z,8Z,11Z,14Z)-N-(4-Hydroxyphenyl)-5,8,11,14-icosatetraenamide