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HCID 1614생성일: 2026년 10월 27일

3,4-Methylenedioxyamphetamine

DL-MDA · 3,4-MDA · Tenamfetamine · AURORA KA-7746 · (±)-MDA solution · mda(pharmaceutical) · N-(2-Methoxyethyl)-αMethylenedioxyamphetamine · 3,4-METHYLENDIOXYAMPHETAMIN

https://huagongshe.com/ko/chemical/1614

3,4-Methylenedioxyamphetamine 분자 구조식

식별자 및 물리적 특성

CAS No.4764-17-4
분자식C10H13NO2
평균 분자량179.22 g/mol
단동위원소 질량179.09462866 g/mol
SMILESCC(N)Cc1ccc2c(c1)OCO2
InChIKeyNGBBVGZWCFBOGO-UHFFFAOYSA-N
PubChem CID1614
ChEMBLCHEMBL6731
ChEBICHEBI:166520
EC No.803-951-7
DTXSIDDTXSID40859958

화학 및 물리적 성질

XLogP1.6
극성 표면적44.5
수소 결합 공여자 수1
수소 결합 수용자 수3
회전 가능 결합 수2
무거운 원자 수13
형식 전하0
복잡도174
LogP(분배 계수)1.64log Kow = 1.64
Color/FormAlmost colorless oil
끓는 점157 °C at 22 mm Hg80-90 °C at 0.2 mm Hgbp22 157°bp0.2 80-90°
DecompositionWhen heated to decomposition it emits toxic fumes of /Nitrogen oxides/.
Dissociation Constants9.67 (at 25 °C)pKa = 9.67 (conjugate acid)
Kovats Retention Index1443143414701495147214801464.614601508.8148414831496.31469.21457.42204
Other Experimental PropertiesCrystals from isopropanol/ether, mp 187-188 °C ... also reported as mp 180-181 °C ... Easily soluble in water, alcohol /Hydrochloride/
녹는점178-179 °C
밀도1.1248 (rough estimate)
굴절률1.5150 (estimate)
인화점9℃
저장 조건2-8°C
pKa(산도 계수)9.94±0.10(Predicted)
물리적 상태liquid
주요 응용법의학 및 독성학
InChI1S/C10H13NO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3
InChIKeyNGBBVGZWCFBOGO-UHFFFAOYSA-N
SMILESNC(C)CC1=CC=C(OCO2)C2=C1
EPA1,3-Benzodioxole-5-ethanamine, .alpha.-methyl- (4764-17-4)

안전 및 규제

GHS 분류DangerH300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
FDA 요건/DEA/ Schedule I shall consist of the drugs and other substances, by whatever official name, common or usual name, chemical name, or brand name designated, listed in this section. Each drug or substance has been assigned the DEA Controlled Substances Code Number set forth opposite it. Unless specifically excepted or unless listed in another schedule, any material, compound, mixture, or preparation, which contains any quantity of the following hallucinogenic substances, or which contains any of its salts, isomers, and salts of isomers whenever the existence of such salts, isomers, and salts of isomers is possible within the specific chemical designation (for purposes of this paragraph only, the term "isomer" includes the optical, position and geometric isomers). 3,4-Methylenedioxyamphetamine (DEA Code Number: 7400) is included on this list.
Hazard Classes and CategoriesAcute Tox. 2 (100%)Skin Irrit. 2 (100%)Eye Irrit. 2 (100%)STOT SE 3 (100%)
처리 방법SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

용도

용도

A metabolite of MDMA. Entactogen; synthetic amphetamine derivative with stimulant and hallucinogenic properties. Controlled substance (hallucinogen).

상호 작용Designer drugs of the amphetamine type (eg, ... MDA) ... have gained popularity and notoriety as rave drugs. ... A variety of adverse effects have been associated with the use/abuse of this class of drugs in humans, including a life-threatening serotonin syndrome, hepatotoxicity, neurotoxicity, and psychopathology.Lethality to both isolated and aggregated mice was determined for graded ip doses of d-amphetamine, dl-4-methoxyamphetamine (PMA), dl-2,5-dimethoxyamphetamine (DMA), dl-2,5-dimethoxy-4-bromoamphetamine (DOB), dl-2,5-dimethoxy-4-methylamphetamine (DOM) and dl-3,4-methylenedioxyamphetamine (MDA). Haloperidol (2.0 mg/kg), propranolol (10 mg/kg) and phenoxybenzamine (30 mg/kg) were tested for ability to antagonize the lethal effects of amphetamine and its derivatives. Considerable protection against amphetamine lethality was produced by haloperidol in both isolated and aggregated mice and by phenoxybenzamine in isolated mice, but propranolol was ineffective. An equivalent degree of protection was not achieved by use of any of the three agents before PMA, DMA or DOB. Protection against DOM was achieved only with phenoxybenzamine and only for isolated mice. Extensive protection against MDA was supplied by both phenoxybenzamine and propranolol for either condition of housing. ...
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ ... In overdose the differences between methamphetamine, 3,4-methylenedioxyamphetamine (MDA), and 3,4-methylenedioxymethamphetamine (MDMA) blur and the clinical presentation is similar to that of amphetamine overdose characterized by tachycardia, hypertension, hyperthermia, diaphoresis, mydriasis, agitation, muscle rigidity, and hyper-reflexia. Death usually results from arrhythmias, hyperthermia or intracerebral haemorrhage. Treatment is aggressive and supportive with careful attention to temperature, blood pressure and seizure control. .../SIGNS AND SYMPTOMS/ Central nervous system effects may be secondary to both sympathetic stimulation and altered perception. Therapeutic or recreational doses may induce feelings of warmth and are purported to promote communication and empathy. Higher doses may induce hallucinations, agitation, delirium, hyperreflexia, or rigidity. Seizures may occur and can reflect either direct CNS stimulation or hypertension induced cerebrovascular hemorrhage. Sympathetic stimulation may induce a state of hyperthermia and agitated delirium. Direct sympathetic stimulation and increased metabolic heat production may be the primary pathophysiologic eventhowever, in many cases, increased muscular activity may be contributory as well. /Phenylethylamines//SIGNS AND SYMPTOMS/ Cardiovascular effects generally reflect sympathetic stimulation. Systolic and diastolic hypertension can be seen. Plus can be variably affected. Tachycardia can be seenhowever if alpha-adrenergic effects predominate, hypertension with reflex bradycardia can occur. /Phenylethylamines//CASE REPORTS/ ... In this case /investigators/ detail a divided dose of 850 mg of MDA ingested within 2 hr and 15 min /which/ was sufficient to cause the death of a 24-year-old male, 4 hr after the final dose. The symptoms of MDA intoxication exhibited by the decedent prior to death closely mimic those of acute amphetamine poisoning: profuse sweating, violent and irrational behavior, and stereotypically compulsive behavior. While the methaqualone may have contributed to the demise of the decedent ... the MDA itself was sufficient to cause death. .../CASE REPORTS/ ...The following symptoms were found in a patient /following Methylenedioxyamphetamine exposure/: sympathomimetic effects, coma, seizures, hyperreflexia, and hyperthermia. The patient's condition was initially stabilized and then deteriorated with uncontrollable hyperthermia, hematologic abnormalities, and coma that culminated in death. ... The concept that this drug is primarily a hallucinogen with mild toxicity is erroneous.
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Acute Exposure/ ... A single 1.8 mg/kg dose of MDA produced 30 to 64% increases in the 5-HT content of frontal cortex from 30 to 120 min after injection and a decrease in 5-HT turnover from 30 min to 8 hr, but had no effect in hippocampus, caudate nucleus, or hypothalamus /of rabbits/. A single 3.6 mg/kg dose of MDA also reduced the turnover of 5-HT in frontal cortex, but this was accompanied by a decrease in 5-HIAA with no increase in 5-HT. The 1.8 and 3.6 mg/kg doses of MDA had no significant or consistent effects on the contents of DA, DOPAC, HVA, and NE in any brain area examined. Chronic administration of MDA (3.6 mg/kg/day for 4 days) failed to produce any evidence of a neurotoxic action on 5-HT neurons. Higher doses could not be employed because the LD50 of MDA was approximately 5 mg/kg. This study has demonstrated that behaviorally effective and nonneurotoxic doses of MDA produce increases in the content and decreases in turnover of 5-HT in frontal cortex that resemble those of other hallucinogens such as LSD and DOM./LABORATORY ANIMALS: Acute Exposure/ ... In rats, /3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxymethamphetamine (MDMA)/ cause large reductions in brain levels of serotonin (5-HT). This study employs immunocytochemistry to characterize the neurotoxic effects of these compounds upon monoaminergic neurons in the rat brain. Two weeks after systemic administration of MDA or MDMA (20 mg/kg, sc, twice daily for 4 d), there is profound loss of serotonergic (5-HT) axons throughout the forebraincatecholamine axons are completely spared. Regional differences in drug toxicity are exemplified by partial sparing of 5-HT axons in hippocampus, lateral hypothalamus, basal forebrain, and in some areas of neocortex. The terminals of 5-HT axons are selectively ablated, while axons of passage and raphe cell bodies are spared. Thickened preterminal fibers exhibit increased staining due to damming-up of neurotransmitter and other axonal constituents. Fine 5-HT axon terminals are extremely vulnerable to these drugs, whereas terminal-like axons with large varicosities survive, raising the possibility that some 5-HT axons may be resistant to the neurotoxic effects. At short survivals, visualization of greatly swollen, fragmented 5-HT axons provides anatomic evidence for degeneration of 5-HT projections. The results establish that MDA and MDMA produce structural damage to 5-HT axon terminals followed by lasting denervation of the forebrain. Both drugs have similar effects, but MDA produces a greater reduction of 5-HT axons than does MDMA at the same dosage. .../LABORATORY ANIMALS: Acute Exposure/ A high intravenous (i.v.) dose of MDA (20 mg/kg) to mongrel dogs elevated body temperature, heart rate, mean arterial pressure and other cardiovascular parameters initially, but only the 1st two remained high. Other functions soon became quite depressed, and death shortly ensued. Arterial pO2 decreased, but pH and pCO2 showed a biphasic response after an initial decrease .../LABORATORY ANIMALS: Acute Exposure/ Body temperature and spontaneous home cage activity were monitored continuously in six male rhesus monkeys via radiotelemetric devices. The subjects were challenged intramuscularly with 0.56-2.4 mg/kg MDMA, 0.56-2.4 mg/kg MDA and 0.1-1.0 mg/kg METH. All three amphetamines significantly elevated temperaturehowever the timecourse of effects differed. The acute effect of METH lasted hours longer than MDA or MDMA and a disruption of nighttime circadian cooling was observed as long as 18 hours after 1.0 mg/kg METH and 1.78-2.4 mg/kg MDA, but not after MDMA. Activity levels were only reliably increased by 0.32 mg/kg METH. It is concluded that while all three substituted amphetamines produce hyperthermia in rhesus monkeys, the effects do not depend on elevated locomotor activity and exhibit differences between compounds. The results highlight physiological risks posed both by recreational use of the amphetamines and by current trials for clinical MDMA use.For more Non-Human Toxicity Excerpts (Complete) data for 3,4-METHYLENEDIOXYAMPHETAMINE (7 total), please visit the HSDB record page.
Populations at Special Risk... Phenylisopropylamines as a class interact with CYP2D6 as substrates and/or inhibitors. Their use may cause metabolic interactions with other drugs that are CYP2D6 substrates, and the potential for polymorphic oxidation via CYP2D6 may be a source of interindividual variation in their abuse liability and toxicity.
Environmental Water ConcentrationsWhile data specific to 3,4-methylenedioxyamphetamine were not located(SRC, 2008), the literature suggests that some pharmaceutically active compounds originating from human and veterinary therapy are not eliminated completely in municipal sewage treatment plants and are therefore discharged into receiving waters(1). Wastewater treatment processes often were not designed to remove them from the effluent(2). Selected organic waste compounds may be degrading to new and more persistent compounds that may be released instead of or in addition to the parent compound(2). Studies have indicated that several polar pharmaceutically active compounds can leach through soils(1).
Antidote and Emergency TreatmentImmediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/Maintain an open airway and assist ventilation if necessary. Treat agitation, seizures, coma, and hyperthermia if they occur. benzodiazepines are usually satisfactory for treatment of agitation, although butyrophenones may also be used. Continuously monitor the temperature, other vital signs, and ECG for a minimum of 6 hours. There is no specific antidote. Hypertension is best treated by sedation and, if this is not effective, a parenteral vasodilator such as phentolamine or nitroprusside. Treat tachycardia with propranolol or esmolol. ... Decontamination: administer activated charcoal orally if conditions are appropriate. Gastric lavage is not necessary after small to moderate ingestions if activated charcoal can be given promptly. Consider whole-bowel irrigation and repeat doses of charcoal after ingestion of drug filled packets ("body stuffers"). Enhanced elimination: Dialysis and hemoperfusion are not effective. Repeat-dose charcoal has not been studied. ... /Amphetamines/Treatment is aggressive and supportive with careful attention to temperature, blood pressure and seizure control. ...
Non-Human Toxicity ValuesLD50 Mouse oral 13,300 ug/kgLD50 Mouse ip 82,300 ug/kgLD50 Mouse ip 68 mg/kg /hydrochloride/LD50 Mouse iv 31,100 ug/kgFor more Non-Human Toxicity Values (Complete) data for 3,4-METHYLENEDIOXYAMPHETAMINE (7 total), please visit the HSDB record page.
수질 위해 등급(WGK)1
운송 번호(UN)2811
독성monkey,LD50,intravenous,6mg/kg (6mg/kg),"Prehled Prumyslove ToxikologieOrganicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 798, 1986.
위험 문구(R)11-23/24/25-39/23/24/25
위험 표시F,T
안전 문구(S)16-36/37-45
포장분류II
위험 등급6.1(a)Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
저장 분류3 - Flammable liquids
유해 물질 데이터4764-17-4(Hazardous Substances Data)